


Destiel Kinktober 2k18

by Substiel



Category: Supernatural
Genre: Aftercare, Alpha Dean, Alpha Dean Winchester, Alpha/Beta/Omega Dynamics, Alternate Universe - Domestic, Alternate Universe - Fantasy, Alternate Universe - High School, Angel Castiel (Supernatural), Angel/Demon Relationship, Angel/Demon Sex, BDSM Scene, Begging, Blind Dean Winchester, Blood As Lube, Blood Drinking, Blood Kink, Blood and Gore, Body Swap, Bondage, Bottom Castiel, Bottom Castiel/Top Dean Winchester, Brat Castiel, CEO Dean Winchester, Castiel in Panties, Castiel is a Tease, Cheating, Collared Castiel, Consensual, Costume Kink, Costume Parties & Masquerades, Costumes, Creature Dean Winchester, Crossdressing, Crossdressing Kink, Daddy Dom Dean Winchester, Daddy Kink, Dark Dean Winchester, Demon Dean Winchester, Dom Dean Winchester, Dom/sub, Frottage, Gags, Gentle Dom Dean Winchester, Hair-pulling, Halloween, Halloween Costumes, Human Castiel, Impala Sex, Jealous Dean Winchester, Knife Play, Knotting, Lactation Kink, Light Bondage, Lingerie, M/M, Male Lactation, Masks, Masochist Castiel (Supernatural), Master Dean Winchester, Master/Slave, Mating, Nymph Castiel, Octo Dean, Octo Dean Winchester, Octopus Dean Winchester, Older Man/Younger Man, Omega Castiel, Omega Castiel/Alpha Dean Winchester, Overstimulation, Possessive Dean Winchester, Power Bottom Castiel, Prisoner Castiel, Prisoner Dean, Punk Castiel, Rape Fantasy, Rape Roleplay, Riding, Rimming, Sadist Dean Winchester, Secretary Castiel, Serial Killer Castiel, Serial Killer Dean Winchester, Sex Slave Castiel (Supernatural), Sex Toys, Sex in a Car, Sex in the Impala, Shy Castiel, Slave Castiel, Spanking, Sub Castiel, Tails, Teen Castiel (Supernatural), Teen Dean Winchester, Teenagers, Temperature Play, Top Dean, Top Dean Winchester, Vampire Dean Winchester, Vibrators, Warlock Castiel (Supernatural), Wing Kink, handjobs
Language: English
Status: Completed
Published: 2018-10-16
Updated: 2018-10-31
Packaged: 2019-08-02 20:14:17
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Underage
Chapters: 31
Words: 37,866
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16311989
Author URL: https://archiveofourown.org/users/Substiel/pseuds/Substiel
Summary: A collection of Destiel one shots for Kinktober.





	1. Masquerade

**Author's Note:**

> I posted these fics separate but decided to put all of them in one.
> 
> Day one of Kinktober - Masks

**Summary for the Chapter:**

> Charlie helps Castiel with his outfit for the masquerade themed school dance. The boy doesn't expect much of anything at the event until Dean asks him for a dance.

The moment his best friend found out about the homecoming theme she went straight to the store, dragging Castiel along with her. She was determined to get the boy laid at the dance because apparently, that’s what normal teenagers do. They snuck in alcohol and had sex in the public restrooms. Gross.

 “Is this really necessary, Charlie?”

 Castiel asked the giddy redhead who had wandered off to the dress section. Charlie had already gotten her outfit the day the theme was announced during school hours. Castiel was definitely not wearing a suit when his best friend suggested it. He was barely comfortable in men’s clothing. Unless his non exist boyfriend lend him some in the near future. There were variations of dresses for the masquerade dance and Castiel didn’t know which one to choose. Of course, Charlie would pick one of the bigger dresses. She picked out a few and shoved them into Castiel’s grasp.

“Try these out. Let me know which one you like best and show me.”

Charlie smiled and shoved him into one of the dressing rooms before turning her attention back to the dresses. Meanwhile, Castiel was struggling to put on these complicated dresses. Some of them were too short for his height or far too tight. Charlie must’ve picked out the tight ones on purpose to show off his bubble butt. 

Finally, he settled with a black dress. It was short enough in the front to show off his creamy thighs and long on the back, forming the tail. The top of the dress only covered his biceps and left his shoulders exposed along with his unmarked pale neck. He looked over the dress in the mirror before exiting the dressing room.

“Charlie! I like this one.”

Castiel called out to her and spread his arms for Charlie to see. He twirled around to show the dress and smiled. He felt good, and by the expression, his best friend was giving him she also agreed.

“It’s perfect!”

Charlie clapped her hands together and moved on to the next item on the list. They had to get heels for Castiel. The boy could barely walk in two-inch heels, but it was obvious Charlie was going to pick out taller ones. Castiel walked back into the dressing room to take off the dress and put his clothes back on. Once he took off the itchy dress he followed Charlie towards the shoe section. The dress was draped over his arm as his eyes wandered around the heels displayed in front of him. 

“Maybe I should just get the plain black ones. I’m sure I’m not going to use them a second time.”

Castiel opened a box to make sure the heels were in there before grabbing it. It was on sale anyways so they wouldn’t need to spend much money. The final thing they needed to get was the mask. There were so many with different shapes and colors Castiel didn’t know which one to choose. Charlie chose a black one filled with blue swirls on it and a blue feather attached to the top.

“A black masquerade mask symbolizes many personality traits like elegant, mysterious, and most importantly seductive. The blue symbolizes loyalty and trustworthy. It suits you.”

Charlie held up the mask to Castiel’s face and loved the way the blue swirls brought out his eyes. He was going to get so much attention at the dance she knew it.

“Let’s buy all this before I change my mind.” 

Castiel said as he grabbed the mask and examined it closely. He felt like he was going to walk in like a witch at the dance. Wearing all black, and there was no doubt his sister would want to do his makeup.

  * \-     -



“Hold still, Castiel.”

“I can’t if you keep poking my eye with the mascara.”

Castiel grumbled in annoyance when he felt his eyes water for the fifth time since Hannah started to do his makeup. It was difficult to have his eyes open for too long when Hannah kept accidentally poking his eye. After a torturous long hour, his sister stepped back and smile proudly at herself.

“Take a look.”

She grabbed the mirror from her dresser and showed Castiel his reflection. He gasped quietly when he didn’t recognize the face that was staring back at him. Hannah had gotten better at makeup since the last time she did it for him. He was wearing black eyeshadow with dramatic eyeliner that would fit his outfit. His lips were a dark red, and he couldn’t wait to see his lipstick on another boy if he got lucky.

“Thank you, Hannah! I’ll call you when I need a ride.”

Castiel hugged her quickly then pulled away to skip to his room. He closed and locked the door behind him to start changing into his outfit for the dance. When he successfully put on the dress and heels he struggled to make his way over to his desk to grab the mask.

“You can do this, Castiel.”

He encouraged himself as he put on the mask. He looked at himself in the reflection and smiled. He loved the way he looked and made a mental note in thanking Charlie for her assistance. He stepped out of his room and headed towards the living room to grab his bag. He had packed an extra pair of shoes just in case he fell flat on his face or got too tired. He gripped the sofa cushion and willed his legs to stop wobbling when his phone buzzed. Charlie was here. He gripped the strap of his bag and headed out of the front door. He quickly made his way into the car and sighed softly at the relief. His feet were already killing him.

“Ready for the night of your life?”

Charlie asked as she turned up the music and started speeding her way towards school. Castiel gripped the edge of his seat and leaned back. He always nagged at his best friend to drive safely, but she hardly listened anyways. He glanced over at her and looked over her outfit with a smile. She had decided on a green dress to match with her green mask. He had totally forgotten what the green mask symbolized as.

They arrived at the school about 10 minutes later with Charlie driving over the speed limit. At least she had her seatbelt on…They both got out of the car and headed inside the school. The dance took place at the gym where it was very humid and a bit smelly. Castiel wrinkled his nose in disgust. Couldn’t they choose somewhere else? Charlie tugged on his arm and dragged him to where the food and drinks are at. She poured him a cup of fruit punch and handed it over to him. He took a whiff of the drink and gagged at the strong smell of alcohol.

“I rather not get grounded for underage drinking.”

Castiel set the cup down and sighed when Charlie chugged hers.

“That was refreshing.”

She took Castiel’s cup and started to sip it in small amounts. She opened her mouth to tell the boy something when Dorothy slid up beside her.

“Hey, you two! I’m glad I spotted you before it got too crowded.”

Dorothy smiled and linked her arms with Charlie.

“Excuse us, Castiel. I hope you don’t mind me stealing Charlie for a bit to dance?”

Castiel shook his head and waved at the couple who practically ran to the dance floor. The DJ had just arrived and was now playing deafening music through the speakers. The sounds of laughter and conversation died down with the music as lots of people started to dance. Castiel stood in the dark corner awkwardly and looked around to spot anyone he knew. Many people walked by him and complimented his outfit. Some boys even winked at him which made him blush.

On the other side of the room, a boy kept trying to catch his eye and smirked whenever he did. The action made Castiel blush even more. He would look back to only notice the boy gone. He never stayed in one place long enough for Castiel to figure him out. At this point, he was looking for the boy when he heard a deep voice behind him.

“May I have this dance?”

The boy asked, all dark and mysterious. He held out his hand, and Castiel took it without hesitation. The two walked to the dance floor, and Castiel was pulled into the boy’s chest. He basically clung onto him as they swayed back and forth. His feet were hurting and the boy seemed to notice this.

“You okay there, sweetheart?”

In response, Castiel only held on tighter and blurted out his name.

“My name is Castiel.”

The boy chuckled quietly. The hot breath against Castiel’s ear made him shiver.

“My name is Dean.”

The boy’s grin made Castiel weak in the knees. Even behind a red mask, he looked hot. He was already thinking about how Dean looked under the clean suit. It was clear the boy had the same thought in mind with those green bedroom eyes checking out Castiel’s curves. The two danced a couple of songs and talked to one another. Mostly random questions to get to know each other better. Just as Castiel knew it; they didn’t have any classes together. The school they attended was a big building so they hardly saw each other. The two wanted to change that.

Castiel was talking about his siblings when Dean pulled him away from the dance floor. He held onto his hand tightly and hoped he wouldn’t trip and fall in front of the cute boy. They exited the building until Dean spotted a big black car parked in front of the school.

“This is my pride and joy.”

Dean said, patting the hood of his car. It truly was beautiful and clean for an old car.

“I love it. Where are we going?”

Castiel asked innocently and tilted his head to the side. Dean merely smirked as he reached behind his head to untie the mask off. Castiel was able to see his face clearly and melted at the sight. He didn’t notice Dean was taking his mask off until he couldn’t feel it on him anymore.

“Beautiful.”

Castiel was about to protest - because how could this hot guy think he’s beautiful? - when Dean grabbed his face and kissed him. His knees buckled and Dean caught him before he collapsed onto the ground. He wrapped his arms around Dean’s neck and kissed him back. Dean opened the back door of the Impala before getting in with Castiel. He was pinned to the car seat by Dean’s muscular figure and moaned when the boy rubbed against him just right.

Castiel tossed his bag in front of the car and they struggled to get his dress off. At one point, Dean bumped his head against the roof of the car. The two of them had a good laugh about it while still trying to take off the dress.

“How did you manage to put this on anyway?”

Dean asked once they finally removed the dress. He tossed it in the front seat before removing Castiel’s short shorts.

“It isn’t that hard.”

He smirked as he raised his hips so that Dean can tug off his shorts. 

“It is for me.”

Dean winked once he started to strip out of his suit. Castiel rubbed his hands at every patch of skin he could reach that was revealed. He really loved what he saw. The muscles contracted under his touch, and he giggled.

“Hold on just one sec.”

Dean held up a finger and pointed towards the front seat. He reached over and opened the glove department to grab the lube, a towel, and condoms. He closed it and set the things next to Castiel.

“I value my baby, and I don’t want to make a mess on her.”

It took awhile for Castiel to figure out Dean meant his car. That makes sense. He raised his hips and Dean tucked the towel underneath him. He gripped the back of his knees and his fingers flexed when he heard Dean open the bottle of lube. He was buzzing with anticipation and shivered when a slicked finger prodded his rim. He dropped his head against the cushion and moaned.

“You’re so tight.”

Dean said, breathlessly. His cock was aching to be inside the smaller boy but refrained himself. He added more fingers to prep Castiel until he was stretched enough. At this point, Castiel was so close to cumming. A bead of sweat streamed down his face and his fingernails were digging into his skin, forming a crescent shape. Dean pulled out his fingers and tugged Castiel’s hands down.

“Stop hurting yourself, sweetheart.”

Dean whispered and leaned in to kiss Castiel deeply. The smaller boy cupped Dean’s cheeks and stroked them gently. His lips gently scraped against Dean’s scruff.

“I-I’m ready.”

Castiel gulped and smiled sweetly at the boy. Dean ripped two condoms open and slipped one on Castiel and himself.

“Okay. Just tell me if it hurts.”

Dean gripped Castiel’s hips and pushed inside the boy. He dropped his head on Castiel’s shoulder and groaned deeply as the heat surrounded his cock. Castiel was so tight and squeezed around his cock so perfectly. He didn’t think both of them were going to last.

Once the pain turned into pleasure for Castiel he pushed back against Dean’s cock. He moaned loudly when Dean started to move. Dean was going slow at first then picked up his pace when Castiel was enjoying himself. He panted heavily as the car moved with his thrusts. He lifted his head from Castiel’s shoulder and groaned at the sight of the smaller boy. Castiel’s face was flushed and his mouth was wide open, letting out loud moans.

A scream was ripped out of him when the head of Dean’s cock nudged his prostate. He came inside the condom and practically turned into goo while Dean kept fucking him. Every thrust hit his prostate and Castiel started to shake with how overly sensitive he was getting. Finally, after a couple more thrusts Dean came with a muffled groan.

He took a couple of minutes to come down from his high before pulling out of Castiel. He took off their condoms and tied them up before wrapping them with the towel. Dean will throw them away once he gets home. For now, he adjusted them until Castiel was sitting in his lap and snuggling him. During the process, Castiel winced a couple of times.

“That was amazing.”

Castiel whispered and hummed quietly. He smiled when he spotted the lipstick on Dean’s face and giggled softly. He laid his head on the boy’s shoulder and closed his eyes with a yawn.

“It was.”

Dean kissed his forehead and chuckled when he heard quiet snores coming from Castiel.


	2. A Warlock’s Blood

**Summary for the Chapter:**

> Dean always comes to Castiel’s shop for pints of blood, and suddenly, he runs out one day.

**Notes for the Chapter:**

> Day 2 of Kinktober - Begging

The bell rang to indicate someone had entered his shop this late at night. Castiel looked up from his work and narrowed his eyes at the man with a strange aura. Definitely not human and not threatening at least. He looked away momentarily when the man turned to look at him. In the corner of his eye, he watched the man head deeper into the store until he was out of sight. The warlock was tensed with the stranger in the store. Especially with him being a supernatural creature. His cat woke up from its nap and plopped down on the counter. She rubbed herself against Castiel’s chest and meowed. Whiskers picked up on his uneasiness and tried to calm him down. He really loved her. He smiled as he scratched her head.

“Excuse me?”

Castiel almost jumped out of his skin when the man appeared right in front of him. He was so distracted with Whiskers he didn’t notice the strange man walking up to his counter. He cleared his throat nervously and looked down at the items in the man’s hand. Three pints of blood. He looked back up at him and noticed some of his features like how pale he is and those beautiful green eyes; hiding a secret behind them on how sad they looked. A vampire. Of course. He hadn’t expected a vampire to come into his shop. Supernatural creatures didn’t dare step foot into his shop. Mostly humans bought this stuff for them. At least the vampire seemed harmless.

“Three pints of blood. That’ll be $9.87.”

Castiel rang up the items and placed them in a plastic bag. People would ask questions on why this man has blood. Any outsider would think everything he has in this shop is fake. Meanwhile, the people who believed in the supernatural just _knew_ it was real.

“I have the money right…here.”

The man checked his many pockets until he found the crumpled ten dollar bill. He smiled nervously and placed it on the counter. Castiel quirked an eyebrow and grabbed it. He flattened out the bill before putting it into the cash register. He counted the coins and held out his hand to give the man his change back.

“Thank you.”

The man said, a bit breathlessly. He stuffed the coins in his pocket and grabbed the plastic bag before dashing out of the shop. Castiel placed his palms on the counter and lifted himself up to look over at the front door. The man was gone already before Castiel could comprehend what was wrong with him. He merely shrugged and forgot about the stranger while he closed up the shop.

During the past few months, the same vampire visited the shop to get three pints of blood. Always three and at night. He was always twitchy and nervous whenever he entered the shop. Never stayed for long. Just enough time to retrieve the blood he needed. Castiel’s initial thought was that the vampire needed feeding. He hasn’t heard anything about vampire killing in this town so the man didn’t kill thankfully. Castiel grew to like him and got comfortable being around him. Sometimes he would offer another pint for free and the vampire looked as if Castiel had given him the world. It was adorable.

One day, Castiel was cleaning out his shop and noticed how the pharmacy didn’t fulfill their delivery. He didn’t think much of it until Dean, the vampire gave him his name the last time he was here, came inside the shop. He was jittery and could barely stand still. The warlock shot up from his spot on the floor and walked towards Dean with a frown. He hadn’t expected him to come by so soon.

“It’s getting stronger.”

Dean nodded to confirm Castiel’s observation the second he stepped into this shop. Vampires were supposed to drink blood directly from the host and Dean was able to resist it for so long. Now that Castiel ran out of blood he didn’t know what to do. He chewed down on his lip as his mind wandered to, what he calls, the no-zone. Dean wouldn’t hurt him, will he? He hoped he was right and even if Dean was able to Castiel could use his magic to hold him off. He took a deep breath before suggesting what he was thinking. 

“Maybe you can drink my blood? I don’t have anymore and it might fulfill your hunger for much longer.”

Dean’s eyes widened at the idea and shook his head. He opened his mouth to deny Castiel’s offer but the warlock beat him to it.

“I’ll be fine, Dean. I’m a powerful warlock. I’ll hold you off if it’s too much, deal?”

Castiel smiled to try and calm Dean down. The vampire was on his last stage on going ballistic and Castiel didn’t want a hunter or someone else to put him down. He took a step forward and cupped Dean’s cheeks.

“Look at me.”

He whispered and waited for the vampire to stare back at him with those green eyes. He kept his smile peaceful and friendly. Finally, Dean nodded slowly and gulped as he was led towards the back of the shop. It would be weird if someone caught them in the middle of...whatever this is. Castiel couldn’t point it out and rather not label it for now.

Dean gripped Castiel’s biceps and panted heavily when his eyes landed on the warlock’s neck. He paused to look at Castiel’s face to make sure he was okay with this. Castiel merely smiled and tilted his head to expose more of his neck. Dean’s breath hitched and leaned in slowly. He opened his mouth and sunk his fangs into the warlock’s flesh. He felt Castiel shiver when he started to feed on him. When the blood hit Dean’s taste buds his eyes fluttered shut and sighed softly at the delicious taste. The blood tasted so much better when it’s directly from the host. Castiel didn’t know how good it would feel for him when Dean feeds. He was high and his tongue felt too thick to form any words. He melted into Dean’s touch and moaned lowly.

When Dean pulled away they were both gripping onto each other and breathing heavily into each other’s mouths. There was still blood on Dean’s lips and Castiel couldn’t help himself. He closed the gap between them and tasted his own blood along with Dean. It was an odd combination but he wasn’t disappointed with the result. Dean kissed him back almost immediately and cradled his head.

“Please please, Dean.”

Castiel broke their kiss to beg Dean to do _something_ about his arousal. It was odd of him to get turned on by something like this, but he wasn’t complaining. He just wanted Dean to touch him. He was already getting too impatient.

“What do you want me to do?”

Dean asked. He was also affected by it when Castiel noticed his pupils were dilated and filled with lust.

“Anything! Just do something, Dean. Please!” 

Castiel rubbed against Dean and huffed when the vampire pinned him against the wall with nearly all his strength. A shot of a pain went through his backside, and he embraced it. With a flick of his wrist, the doors to the shop locked and he tugged Dean towards the room he sleeps in. He hardly left his shop unless he was hungry, needed some supplies, or plan on visiting his family. He wasn’t very social and didn’t like going out that much. That would probably change with Dean now.

Castiel pushed Dean on the bed and climbed onto his lap. He moaned softly when he felt the man’s cock rub against the crack of his ass.

“I want that impressive cock in me.”

Castiel’s tone wasn’t demanding and made it known when he looked up at the man through his eyelashes. If Dean didn’t want this then he would accept that. Doesn’t mean he can’t beg for it. He’ll gladly do it.

“We need to take off our clothes.”

Dean smirked and waited for Castiel to get up, but the warlock shook his head. He held out his hand and muttered a spell, Dean couldn’t hear, under his breath. Both were naked and Castiel had lube in his hand. Dean made a small noise of surprise and glared at Castiel playfully. If the warlock kept doing that Dean would never get used to it, ever.

“I’m impatient.”

Castiel stated before uncapping the lube. He slicked his fingers up with the gel and raised onto his knees to reach behind him. He did this a couple of times and knew how to prep himself quickly, but with Dean’s length, he would need to take his time. He sucked his bottom lip in between his teeth when he pushed one finger inside his hole.

“You look so good like this.”

Dean whispered quietly as he rubbed Castiel’s thighs. The praise made him feel warm, and he grew more confident in his movements. He added another finger and rode both of them until he turned into a moaning mess.

“Oh fuck!”

Castiel jumped when Dean gripped his ass cheeks to spread them. His fingers were able to go all the way in. He thrust them in and out a couple of times before pulling them out. He slicked up Dean’s cock and positioned the head of his cock on Castiel’s hole. Dean watched, memorized of how beautiful the warlock looked when he slid down on his cock. Castiel felt so full with Dean’s cock inside him.

“Fuck me, please! Show me what you got, big boy.”

The words encouraged Dean to grip his hips and thrust upwards. Castiel shouted when his cock nudged his prostate. The position they’re in made Castiel’s thighs shake when the head of Dean’s cock kept assaulting his prostate. He wrapped his arms around his neck and dug his fingernails into Dean’s back.

“Yes, just like that. Faster. Keep going.”

Castiel’s breathless response was fulfilled when Dean picked up his pace. The warlock ran his fingers through Dean’s dirty blonde hair and begged quietly until he felt his peak. The vampire’s powerful thrusts sent him over the edge, and he came on both of their stomachs. Dean was right behind him when he clenched around his cock perfectly. He shivered when he felt Dean’s warm cum fill him up. He moaned quietly and smiled lazily.

When Castiel looked into Dean’s green eyes he noticed how peaceful and happy he looked. It was the very first time he saw the vampire this relaxed. He felt accomplished.


	3. The CEO’s Secret

**Summary for the Chapter:**

> Dean couldn’t wait until his meeting is over. He just knew Castiel was waiting for him.

**Notes for the Chapter:**

> Day 3 of Kinktober - Temperature Play
> 
> This is my first time writing Temperature Play, so I’m sorry if it’s inaccurate.

The meeting was getting too long for Dean. Maybe because of what he’s planning to do after the meeting, and not to mention, he keeps glancing at the clock every five minutes. Every minute was dragged out and Dean was getting too impatient. He bounced his leg and clenched his hands into fists. During his boredom, he spaced out until he heard his name. He blinked and looked up in confusion. Mr. Adler scrunched up his nose and shook his head in disappointment.

“Pay attention, Mr. Winchester. You’re up.”

He gestured towards the front of the conference room and smirked. Dean glared right back at him and didn’t even hide his hatred towards the man. Everyone knew he wasn’t very fond of Zachariah. People just thought because of how unmannerly the man could be towards the CEO. They didn’t know the real truth. None of them did because Dean liked to keep his life private. The reason why he hated the man so much was because Zachariah always intends to flirt with Castiel.

“My apologies. I’m a bit distracted. It won’t happen again.”

Dean forced a smile and hoped it looked real enough for the people in the room to believe him. Even though he hates Zachariah, he never started a scene. Castiel wouldn’t like that. Especially about the topic, they would fight over.

Dean stood up from his seat and walked towards the front of the room. His smile was relaxed and peaceful which meant only one thing; the conference was about to be over. He cleared his throat and turned around to look at the data on the board. He tapped his chin and looked over it a couple of times until he made his decision.

“I love the work you all did. Bravo. I’ll look more into it first thing in the morning then I’ll tell you my final decision. Deal?”

Dean looked around and smiled when the people agreed with his idea.

“Great! You are dismissed.”

Everybody looked relieved. At least he wasn’t the only one who wanted this meeting to end already. He nodded at his coworkers and shook their hands before they left. Zachariah was the last person in the room with Dean and decided to stick around to chat with him. Of all days, he had to do it now?

“Do you have a moment of your time?”

Zachariah didn’t bother to shake Dean’s hand and stood a few inches away from the door.

“Actually, I don’t. I have a lot of work to do, Mr. Adler.” 

“It’ll only take a minute.”

A minute was far too much in his opinion. He was getting restless and rather be with Castiel at this moment. If he stayed out too long he didn’t think Castiel would like that. Yet, Zachariah stood his ground and was too stubborn to drop this. Finally, Dean sighed and nodded. He didn’t need to drag this out.

Zachariah went on a full explanation on why they shouldn’t accept the deal. Dean just pretended he was listening and nodded every once in a while. He meant it when he said he was going to look into it tomorrow. His mind kept wandering off to Castiel. The younger man who is being kept in a cold room right now. Dean planned out his timing and the temperature before he left. He even double checks to make sure. He didn’t intend to actually hurt Castiel and hoped that the younger man was enjoying himself right now. 

“That’s great. I’ll look into your explanation and data. Thank you for your reasoning.”

It took Dean a couple of seconds to figure out that Zachariah stopped talking. He blurted out a random response and smiled in a polite manner. He gestured towards the door and waited for the man to exit. He sighed heavily and tugged on his collar to loosen it up a bit. He left the conference room and headed towards his office. 

“Hey, Charlie.”

Dean greeted his secretary and smiled at her when she waved at him. She was currently on a phone call and oblivious to what Dean’s plans are for the rest of the day. When he entered his classroom he made sure it was locked. If Charlie needed something then Dean would hear the knocking and pause their scene momentarily to see what his secretary needed. He stripped out of his suit jacket and tie before going into the small room he had in his office. It was very cold, compared to him sweating a couple of minutes ago in the conference room.

Castiel stood, naked, in the middle of the room. His wrists were cuffed to the ceiling, and he was shivering but his cock was hard. Dean took a minute to take in the view as he started to roll up his sleeves. He changed the temperature of the room before walking towards Castiel. He reached out for the tray with a set of tools for his prize. This was the second time they were playing this scene since Castiel had gotten sick the first time. Dean felt bad, but Castiel loved it. It took time for the younger man to convince Dean he wanted to do it again. Not to mention, they had to plan it out so that Castiel wouldn’t get sick again.

“Sorry for taking so long, sweetheart. Zachariah wanted to talk to me.”

Dean rolled his eyes and huffed angrily just by thinking about the man. He shook his head to get rid of his thoughts and turned his full attention on Castiel.

“Remember to say honey bee when it gets too much, okay?”

He waited for Castiel to nod before grabbing the candle and lighter. He lit up the candle and watched the fire dance. He held up the candle towards Castiel’s chest and tilted it. The fire burnt the wax and the drops landed on Castiel’s chest. The younger man hissed and moaned quietly at the sensation. The noises he made went straight to Dean’s cock. The hot and cold combined have Castiel’s body a rush of sensations he enjoyed very much.

Dean wrapped his hand around Castiel’s cock and stroked him while he kept burning him with the candle. The younger man tugged on the cuffs and panted heavily. The room was suddenly getting too warm for him and whined when a drop of wax landed on his hardened nipple. Dean reached out for the tray again to grab the ice cube. It became much smaller since the last time he was here but was still effective. He placed the ice cube on Castiel’s other nipple and smirked at the response he received. The younger man jumped and opened his eyes to give Dean a surprised look. He wasn’t expecting that so soon.

“Can I cum, sir?”

Castiel chewed on his bottom lip and pleaded with his puppy eyes. Dean took a couple of seconds to think about his request.

“Yes, baby. You did so well.”

Dean blew the candle out and deposit the items. He ignored his own arousal to pay attention to Castiel. He gripped the younger man’s cock again and stroked him. He dug his thumbnail into the slit then rubbed over it with the pad of his finger. He loved how sensitive Castiel was and praised him when the man came with his touch only.

“Good boy.” 

Dean grinned as he held up his fingers towards Castiel’s lips.

“Suck.”

He demanded. Castiel held his gaze as he wrapped his pink lips around Dean’s fingers slicked with cum. He moaned loudly as he licked up all his cum. Once Dean’s hand was cleansed, he unlocked the cuffs and rubbed the red marks that formed on Castiel’s wrists. He grabbed his hand and tugged him out of the room.

Dean locked the room behind them before grabbing the duffle bag that was on his desk. He opened the bag and took out Castiel’s clothes. He turned towards his lover and helped him into his clothes.

“You did so well for me, baby. I love you.”

Dean grabbed Castiel’s chin and kissed him softly. He beckoned him over to his desk and sat down on the leather chair. Castiel smiled tiredly and climbed onto Dean’s lap. He laid his head on the man’s chest and drank the water Dean offered him. The older man hand fed him and patted his hair as they held onto each other.

“Thank you for agreeing to do this, Dean. I love you.”

Castiel’s response was faint but Dean was able to hear it. He grinned and felt proud for making his lover happy.


	4. Best Tamer

**Summary for the Chapter:**

> Castiel doesn’t know how to ask but knows what he has to do.

**Notes for the Chapter:**

> Day 4 of Kinktober - Spanking

Sam thought it was a great idea to throw a party for his son at Dean and Castiel’s house. He had burst in through the front door without warning. At least he hadn’t walked into them doing...inappropriate stuff...again. The older Winchester was already thinking about how much of a bad idea it was to let Sam have a key.

“Can I throw a party for Mary here?”

Sam had asked, and how could he deny his favorite brother and niece? Yes, Dean knows they’re his only brother and niece thank you very much, Sam.

That’s how Dean and Castiel ended up planning a date and buying directions for the party. Castiel loved Mary just as much as Dean, so he knew his boyfriend wouldn’t be angry about the party. Dean, being the best uncle he can be, got the best decorations of the little mermaid. He knew how much Mary loved Ariel and Dean always watched the movies with her. No matter how much he gets tired of them. He always smiles through the whole film and sings along with his niece.

The day of the party left the whole family busy. Meanwhile, Mary was playing around in the bouncy house in the backyard. Dean was cooking the food and Castiel was helping out Sam and Jess with the decorations. By the time he was finishing cooking all of the food Dean barely had any time to actually get ready and change into nice clothes. Guests were already arriving and ringing the doorbell. He was about to step out of the kitchen when Castiel stopped him by the doorway.

“You’re not going out there. You look like a sweaty lumberjack.”

Castiel gestured towards Dean with a shake of his head. He turned his boyfriend around and pushed him towards the hallway.

“But people are already here. I don’t have time.”

Castiel ignores Dean’s protest and followed him all the way to the master bedroom. He leaned against the doorway and arched a brow.

“I’m not letting you go out there until you’re clean and wearing something nice. I’ll go tell them you’re busy getting ready, okay?”

Castiel placed his hands on his hips and waited for Dean to nod. He smiled and walked forward to place a kiss on Dean’s cheek.

“You worked so hard today. Maybe after the party, I can reward you.”

Castiel teased and winked. Dean gulped at the suggestion and nodded like he was in a trance. He leaned in to kiss his boyfriend deeply and whined when the man pulled away after a while. He watched him walked away until the man was out of view. He hated how Castiel can get him all riled up easily. Not to mention, all the teasing he does to get his way. Castiel had stayed in the hallway and waited until he heard the bathroom door shut and the water running. He smiled in victory and walked back to the living room where the guests were at. He greeted them and led them to the backyard where Sam and Jess were at.

Jody and Donna were the first to arrived and smiled in greeting at the loving couple. Castiel stayed in the living room and waited for more people to arrive early. He kept glancing at the hallway to see if Dean would come out at any minute. He always felt awkward in parties and usually stuck to Dean’s side. The man was the more social one and just knew how to keep a conversation no matter what. Castiel would rather listen to him talk instead of being here but this was for Mary. He loved her as if she was his own child. He could pull through for her.

A couple of more people, he didn’t know and never saw, arrived. They introduced themselves as Sam’s friends. One of them even tried to flirt with Castiel. He couldn’t help but blush and giggle softly. Not because of the friend, because of how Dean would react if he saw this. Just by thinking about it made Castiel hot all over which gave him a splendid idea. He smirked as he led Sam’s friends to the backyard and stuck around. He served them drinks and food. Castiel mostly ignored the flirty guest who tried to get his attention. He was waiting for Dean’s arrival.

About forty minutes later Castiel started to get bored. He glanced at his phone to check the time. More people wouldn’t be arriving until three pm which shouldn’t be long. He finally heard the sliding door and bit his lip as he started to get nervous. The feeling only increased when he heard Dean’s deep voice greeting Jody and Donna. It was now or never. He lifted his head and walked towards the group of friends. They all immediately looked at the flirty person; who was named Balthazar, Castiel soon learned.

“Do you need anything else?” 

He asked shyly. He hoped his voice didn’t shake from asking the question. He was always shy around new people and hoped he wouldn’t puke at how nervous he felt. He looked around the group and smiled when he made eye contact with Balthazar. He dipped his head and batted his eyelashes at the man. Dean always said he looked pretty when he did that.

“Maybe your number?”

Balthazar asked with a confident grin on his face. His friends snickered and looked at Castiel in anticipation. They were obviously waiting for him to answer and give him his number.

“I don’t give my phone number out to just anyone, silly.”

Castiel giggled and felt his cheeks heat up. The attention he was receiving from the group made him uneasy. He was always the outsider. The person who no one cared about and paid attention to. Maybe that’s why he ended up with the first man he fell in love with. Dean was funny, talkative, interesting, and attractive. Everything Castiel wasn’t.

“How about I take you out to dinner? Maybe that’ll change your mind?”

Castiel was ripped out of his thoughts when the man suggested dinner. He looked like he was thinking about it even though he knows his answer.

“Who else is going? Are you bringing your friends?”

He was playing the oblivious part and felt successful when the group snorted. Everyone except Balthazar who was shaking his head. Castiel placed his hands on his hips and pouted.

“What’s so funny? It’s just a simple question.”

“I meant just you and I. Like a date.”

Balthazar gesture between them and smiled when he saw Castiel blush again. He tried to play it off by just giggling. One of the things he didn’t like about himself was that he could never say no. He always tried to avoid people trying to ask him out. He was always afraid he would run into someone who wouldn’t take no as an answer. He was about to respond when he felt someone grab his arm. The grip was hard enough to bruise. 

“Good evening, gentlemen. Don’t mind if I borrow my _boyfriend_ for a minute?” 

Dean glared at Balthazar. Castiel could practically feel Dean radiating jealousy when he dragged him away from the group before they could comprehend what just happened. He dragged Castiel into the house and slid the door shut behind him.

“What was that back there?”

Dean crossed his arms and glared down at Castiel’s innocent face. Now that they were alone he had the confidence he needed. They stared at each other in silence when Castiel finally answered him.

“I don’t know what you’re talking about, Dean. We were just having a friendly conversation.”

He ducked his head to look up at Dean through his long eyelashes. Dean growled softly as he grabbed Castiel again and dragged him into their bedroom and locked the door behind him. He took a couple of deep breaths to calm down his anger before turning his full attention on Castiel. He sat down on the bed and patted his lap.

“Get over my knee.”

Dean said in the calmest tone in the situation they’re in. Castiel was shaking with excitement and obeyed Dean. He clenched his hands into fists and bit his lip. Dean pulled down Castiel’s jeans and boxers. The first smack was unexpected but soft. Castiel jumped and moaned softly. Dean hadn’t spanked him for a long time. Castiel missed this. He shoved his ass against Dean’s hand, asking for more.

“I want you counting.”

Came Dean’s raspy voice. He was already affected by Castiel’s response and wanted to pull more noises like that from him. He waited for his boyfriend to nod before continuing the punishment. The next smack was a bit harder.

“Two!”

Castiel gripped Dean’s jeans and panted heavily. He was already hard and his boyfriend just started. Dean laid smacks on both Castiel’s ass cheeks and sometimes rained them down on his hole. One smack harder than the one before. Castiel lost count and started to enjoy himself instead. He whimpered and started to squirm in Dean’s grasp. He didn’t know if he was trying to squirm away from the smacks or push back against them. He was sweating and his cock was leaking. He rubbed against the denim of Dean’s jeans for friction and moaned softly. It wasn’t enough but he knew Dean would only let him cum like this.

His hands were printed red into Castiel’s skin. It was like a way of marking him. A wave of possessive took over Dean at the idea. He needed to do this more often if his boyfriend kept acting like a brat. He spread Castiel’s ass cheeks and rubbed his rim with a dry finger. The new sensation made Castiel gasp and cum all over Dean’s lap. He manhandled Castiel to sit onto his lap, he hissed when his sore ass rubbed against the denim and started to kiss the tears away.

“It’s okay, baby. You received your punishment so well.”

Dean praised him and felt his heart swell when Castiel gave him a shy smile. He looked like he was glowing after his punishment. Dean rubbed the red marks that were on Castiel’s ass and chuckled softly.

“You could’ve just asked instead of making me jealous.”

Dean pulled away to look at Castiel’s sheepish expression.

“I’m sorry. I didn’t know how to ask.”

Castiel whispered quietly and nuzzled Dean to hide his burning face. Dean merely smiled at how adorable his boyfriend can be and kissed his forehead.


	5. Nowhere to Hide, Angel

**Summary for the Chapter:**

> Their sex life became a lot more interesting with each idea they come up with.

**Notes for the Chapter:**

> Day 5 of Kinktober - Sadism/Masochism
> 
> All of this is consensual. It’s just a fantasy. This is my first time writing a rape fantasy, so I hope you enjoy.

Castiel ran down the dark alleyway and looked around every corner. His white downy wings were dragging behind him which made him a lot slower. He flapped his wings and jumped to grab the railing. Before he could pull himself up someone grabbed his ankle and pulled him down. His hands slipped and he collided with a strong figure behind him. He whined when his wings folded in awkward angles and struggled against the man’s hold.

“Where are you going, little angel?”

Dean rasped against his ear. The hot breath made Castiel shiver as he tried to get out of the demon’s hold. Ever since Dean bared the mark of Cain, he was never the same. Now that he died and came back as a demon...Castiel was trying to accept his fate. Of course, he still hasn’t and never believed in the demon’s lies. Dean never loved him and never will in this form.

“Let me go!”

Castiel screamed and struggled even more. He froze and suck in a sharp breath when he felt Dean’s tail wiggling against his stomach. The tail slipped into his trousers and it hit the switch. Castiel elbowed Dean on the cheat and managed to escape when the demon released his grip on him. His stupid broken wings, he didn’t like thinking about, never got him far. Why wasn’t anyone here? Maybe that was a good idea since Castiel’s wings were out in the open. He didn’t get far. Dean still cached up to him and pinned him to the ground. Castiel groaned when the side of his face was plastered against the concrete. 

“What are you going to do to me?”

The only thing trembling more than the angel’s voice was his wings. Normally he’d have them hidden away, especially in front of a demon, but they were sore and sensitive. Needless to say, Dean wasn’t gentle when he tugged on them. The demon chuckled darkly as he reached into his back pocket for the Enochian handcuffs. This would be fun. He snapped one on Castiel and snapped the other cuff on the pole. The little angel wouldn’t be running away anytime soon.

“I’m going to fuck you so hard. I’m going to make you scream my name, baby.”

Dean growled softly in his ear and Castiel shivered in fear. He shook his head and tugged on the handcuff that burned against his wrist. The demon took out the first blade and held it to Castiel’s throat.

“Please, Dean. Don’t do this.”

Castiel cried quietly and whined even louder when Dean cut his collarbone. The droplets of blood fell onto the floor as Dean continued to rip his white dress shirt. He was glad for not wearing the trench coat. He wouldn’t forgive Dean if he messed up his trench coat.

“You want this, you bitch. I know you do. You would spread your legs just for anyone.” 

Castiel shook his head at Dean’s statement and gasped when the blade cut him on his stomach. His nails scraped against the concrete until they started to bleed. He tried to keep his moans in the best he can when Dean kept carving into his skin. He wouldn’t give the demon the satisfaction.

“Don’t lie to me. I see how you look at me. Well, Human me. As a demon, you look at me with disgust. Did you move on? Decided to woo the other Winchester because of how broken I am?”

Dean grabbed a handful of Castiel’s hair and pulled hard to lift the angel’s head. He felt like he had a massive headache from the strength Dean has. Just by the thought of the demon being so strong made his cock jump. He squeezed his eyes shut and felt ashamed at being turned on by just one single thought. 

“N-no! Sam is a friend.”

Castiel said quietly. Dean had to lean in to hear the angel. He scoffed and rolled his eyes.

“That’s what they all say. Don’t worry, bitch. I’ll make you forget about him. I’ll make you forget about everything else. You’ll just feel me plowing into you.”

Dean promised and let go of Castiel’s hair. He unzipped his trousers and pulled them down to reveal the angel’s perfect ass. He squeezed the globes of his ass tightly and chuckled when Castiel jumped.

“Stay still, whore.” 

Dean rubbed a dry finger on Castiel’s hole and the angel tried to shy away from the touch. The action made Dean angry by the way he made a nice clean cut on his bicep. Castiel cried out and covered the wound. The new position made his arm wobble and he collapsed onto the ground. The pleasure and pain mixed together so good Castiel was hard by the time Dean entered a dry finger into his hole.

“You enjoy this, don’t you? You’re such a slut for it.”

Dean moaned and wrapped a hand around Castiel’s cock. He stroked it and squeezed around the head. The angel squeaked and thrust into the demon’s fist without thinking. Dean let go of his cock and smirked when Castiel whined at the loss of contact.

“Don’t worry, baby. I’ll take care of you.” 

Dean patted Castiel’s back and smiled when the angel leaned into the touch. He was almost there to breaking the angel completely. When he added a second finger Castiel winced; again, he tried to get away. Dean sighed heavily and took out his fingers to only stuff three inside Castiel’s mouth. 

“Suck them, bitch. It’s the only kind of lube you’ll get.”

Castiel looked over his shoulder at Dean with watery eyes and obeyed his command. He regretted it when those green eyes flickered black. He turned away the best he could. He twirled his tongue around Dean’s fingers and gagged when the demon pushed them in too far. 

“Good boy.” 

Dean patted Castiel’s hair lovingly before taking his fingers out. He thrust them back inside his hole and crooked them until he found his prostate.

“Ah!” 

Castiel jumped and thrust his ass back against the fingers that were rubbing against his prostate. He breathed heavily and leaned his forehead on the ground. He was covered in sweat, tears, and blood. How more filthy can he be? He immediately regretted that thought when he felt Dean’s tail rub against his glands. His wings quivered from the touch and dropped in submission as the oil started to cover them. It felt so good it almost overpowered his disgust and guilt.

“Stop thinking, sweetheart. If you keep your mind wandering I’ll make it hurt.”

Dean threatened. He inserted his last slicked finger and spread Castiel’s knees with his leg. 

“Please stop this, Dean. This is too far.” 

Castiel sobbed when Dean’s tail tug deeper into his wings. His hole clenched around nothing when Dean retracted his fingers.

“Shut up. Now, be a good little bitch and take my cock like the slut you are.” 

Dean unzipped his jeans and took out his cock with a moan. Castiel’s body shook with the noise and felt his heavy cock leak in between his legs. He started to struggle again and hissed every time the Enochian handcuff burned his wrist. He didn’t care. He just wanted to leave.

“Stay still, bitch.” 

Dean placed his foot on the back of Castiel’s neck and pinned his head to the ground. The angel whimpered and scrunched up his nose when he thought about the boot mark that will be imprinted on his neck. If he were human Dean would’ve been able to break his neck.

“Nowhere to run now. How do you feel? Being this powerless.”

Dean chuckled darkly. He brought a hand down on Castiel’s ass which made the angel jump from the smack. A red handprint started to form as Dean rubbed his cock against the crack of Castiel’s ass. The angel squeezed his eyes shut and tried to lean away the best he could in his position. He pleaded for Dean to stop. He was so powerless he felt defeated. How did he let the demon have the upper hand? He was ashamed of himself. He couldn’t get far until the demon started to plow into him. It was fast and hard. Dean showed no mercy and increased the pressure where his foot was pinning Castiel down. His tail wandered over to the most sensitive parts of the angel’s wings which made Castiel scream in pleasure.

“Dean!” 

Castiel couldn’t form any other words except the demon’s name. His cheek and knees were scraping against the concrete as Dean’s thrusts moved him. He was so lost in the pain and pleasure he didn’t notice Dean grabbing his first blade to make more marks. He groaned loudly when the demon made a cut right beneath his wings. The edge of the blade dug into his scars, not deep enough to break the skin, where Dean had carved in his initials. The scar was big and written underneath the middle of his wings. The day Dean decided he wanted the angel.

“You feel that right there? You belong to me. You always have. No matter what.” 

Dean increased the force of his thrusts until Castiel came all over the floor. The angel went limp and sobbed through his orgasm as Dean continued his movements. At the point, Castiel was getting sensitive, and his body started to shake from the overstimulation. His thighs started to wobble and he couldn’t stop the moans coming from his mouth. His limp cock twitched in excitement but he was too tired.

“You enjoyed this, didn’t you? You sick fuck. The chasing you around part was kinda fun. Maybe we can do that again.”

With one final thrust, Dean pulled out and stroked his cock until it spurted strips of cum onto Castiel’s wings. They were also limp and couldn’t do anything but lay there as they got covered in the demon’s semen. 

“Thanks for the fuck.”

Dean lifted his foot and stood up from the floor. Castiel heard the footsteps fade away and let out a sigh. He tried to sit up but was stopped when the Enochian handcuff tugged him down. A couple of seconds later warm hands clasped around his hand and removed the handcuff. His watery eyes looked up into Dean’s green ones full of love. The demon put the handcuffs inside his pocket and wrapped his arms around Castiel. He kissed the tears away and ran his fingers through the dark hair.

The angel felt warm and a soft bed was underneath the pair. Dean teleported them back to the hotel they were staying at with his demonic powers. It was going to take Castiel time to get used to it. Now he knew why Dean didn’t like it when he used his wings to teleport. Now they weren’t capable of flying anymore.

“You did so well for me, angel.”

Dean whispered as he placed a finger under Castiel’s chin to lift his head up. He leaned in to kiss his lips lovingly. Castiel sighed into the intoxicating kiss and leaned into Dean’s touch.

“I didn’t hurt you, right?”

Dean asked, concern filling his eyes. Castiel shook his head and smiled. 

“I loved it. Every part of it.”

Castiel laid his head on Dean’s chest and gripped his shirt.

“I want a bath, please. Maybe some cupcakes too.”

Castiel smiled sweetly when he heard Dean chuckle quietly and felt him nod his head. He held onto the demon tightly when he carried him to the bathroom. It wasn’t the best like in the bunker but it was something. Dean was kind enough to bring the bubble bath bottle Castiel loved so much. When the demon placed him down on the tub; Castiel leaned his head against the wall and sighed as Dean turned on the warm water. It felt good against his skin. He closed his eyes and smiled happily. A couple of minutes later he felt something nudge his lips. He opened his eyes and immediately opened his mouth to bite into the cupcake. The tub was halfway filled and full of bubbles already. 

“Thank you, Dean.”

“You deserve this, sweetheart. I love you.” 

Dean ruffled Castiel’s hair and kissed his forehead. No matter how much he changed as a demon, Castiel will always love him. They were dancing around each other for years and eventually got together when Dean became a demon. At least they will be together for centuries if people don’t decide to kill them.

“I love you too, Dean.”

Castiel grabbed his hand and intertwined their fingers.

“We should do that again.”

The angel suggested and looked up at Dean almost shyly. He thought about this role-play for a while and decided to bring it up. Of course, Dean wanted to plan everything out to make sure he didn’t hurt his angel. 

“This time we’re doing one of my ideas.”

Castiel nodded eagerly and waited for Dean’s idea.

“How do you feel about wearing a police officer costume?”

Dean arched a brow and waited for Castiel’s answer. He was never ashamed or shy about what he wanted which made Castiel love him even more. Their sex life became a lot more interesting with Dean’s great ideas.

“I’ll definitely wear one.”


	6. Who’s in Charge, Now?

**Summary for the Chapter:**

> Castiel has a crush on his boyfriend’s dad.

**Notes for the Chapter:**

> Day 6 of Kinktober - Daddy

Castiel played with his lip ring as he slouched on the couch he was sitting on. He was mostly focused on the screen in front of him when Samandriel tried to snuggle into his side. He ignore the whiny boy when an intense scene came on. Samandriel huffed at how engrossed Castiel was in the movie and gave up. He crossed his arms over his chest and scooted away from Castiel who didn’t even notice.

When the movie ended Castiel stretched his arms out over his head and groaned. He smacked his lips and rubbed over his cold arms. It was always so cold in his boyfriend’s house and later on, he learned that his dad liked it that way. Dean was a very attractive man for his age Castiel had to admit. It was too bad he wasn’t here today.

The moment he laid eyes on the man Dean became the number one on his list he would cheat on Samandriel with. He always snuck in glances and checked out the older man. The boy full of tattoos and piercings was into his boyfriend’s father. Just by the thought of Dean made Castiel smile; other than his good looks, Dean had a great personality. He had so much in common with Castiel. He was so lost in thought he didn’t know Samandriel was reaching out for him.

 “Let’s go to bed, yeah?“

Samandriel winked suggestively, meaning he was in the mood. Castiel bit back a sigh. Samandriel was a lovely boy but sex wasn’t as much fun with him anymore. When Castiel tried to change it up and explore his kinks Samandriel had thought it was weird. After that Castiel never mentioned it again and barely wanted to do anything with the boy. The only reason why he was with him was so that he could see Dean. He knew he was using the boy but didn’t really care at this point. He knew how Samandriel looked at this one boy in the class they share. He didn’t even get jealous which means he didn’t have any feelings for Samandriel anymore.

“Sure. I’ll be right there. I just need to change.”

Castiel gestured towards the duffle bag and smiled. Samandriel nodded and stood up from the couch to walk towards his bedroom. The boy sighed and slumped on the couch. How was he going to get out of this sticky situation? He already knew he can’t go home since he told Samandriel about his family. They didn’t approve of his looks and interests. Nobody really bothered to get to know him because he was always labeled as the punk who no one talks to.

Except for Dean.

The man always seemed to be interested in talking to Castiel. Always having the best topics to talk about and never sounding forced. It was definitely more than a crush. It took some time for Castiel to accept it, but he eventually did. How could someone not love Dean? He remembered the first time he meant him.

_Castiel and Samandriel were in his boyfriend’s room when they heard a deep voice call out his name. Samandriel’s eyes had widened in fear when his dad came back so soon. Castiel, being the tough one in their relationship, decided to finally meet Samandriel’s dad. What’s the worst that can happen? He tugged on his boyfriend’s hand and stumbled out of the room with him._

_“There you are. Who’s this?”_

_Dean asked, gazing at Castiel with interest. The boy wraps his arm around Samandriel and pulls him close with a smirk._

_“I’m his boyfriend.”_

_Castiel said proudly and glanced over at Samandriel wh blushed and nodded in agreement. Needless to say, that’s when Castiel’s crush on Dean started. It didn’t help that the older man was always wearing a suit._

“Don’t think about him. You’ll just make yourself feel lonely.”

Castiel scoffed to himself as he stood up and grabbed his duffle bag. He headed towards the bathroom to change into his sweatpants. He balled up his skinny jeans and stuffed them into his bag. He turned on the sink water and wiped off the eyeliner. It took a while for him to take it off, but he hoped his time in the bathroom meant Samandriel fell asleep. He dried his face with the towel and looked at the mirror one more time before exiting the bathroom.

Before he could retire to Samandriel’s room he hears the front door open. He glanced between the door and the end of the hallway before deciding. He sneaks around the corner and peeked into the living room where Dean is. The sight of the older man made Castiel lick his lips. He thought for a couple of minutes to form a plan before just winging it. He headed into the living room and waved at Dean as he made his way towards the front door.

“Hey, Cas. Where are you going?”

Dean greeted him by returning the wave.

“I can’t sleep. I’m going to take a walk.”

Castiel immediately knew that glint in Dean’s eyes he has right now. It showed up every time he had a thought in mind. Castiel just hoped he would make that thought into reality.

“I have something else in mind we can do to make you nice and tired.”

Dean smirked and wiggled his eyebrows. It was like he had read Castiel’s mind. The boy shouldn’t do this. Especially with Samandriel in the house but good god what other chance will he get? 

That’s how they ended up making out in Dean’s room. With that seductive deep voice the man had and Castiel’s non-existent sex life for the past month. They ripped each other’s clothes off and practically devoured each other’s mouth. Months of sexual intention and teasing all poured into that make out session. Once Dean was naked, Castiel tried to push him onto his back but damn he was strong. 

“Keep up the act and I’ll have to tie you up, sweetheart.”

Dean growled playfully and flipped their position to pin Castiel to the bed. The thought of being tied up made his cock twitch in interest. He had never bottomed before and wasn’t really looking forward to it even though his cock thought otherwise. He wrapped his arms around Dean’s neck and brought his head down to kiss him. He tried to take control again but failed miserably when Dean started to roll his hips. He moaned quietly.

“You’re not in charge anymore, pretty boy.”

Dean winked. He tried to distract Castiel, who was able to protest and felt around for the tie he was wearing before. He grabbed Castiel’s wrists and tied them to the headboard of the bed. The boy barely registered what happened when he started to tug his wrists.

“Relax baby. I got you. Try and keep yourself quiet.” 

He had totally forgotten where they were at. He didn’t care though because Dean was mouthing at his neck. He threw his head back and gasped quietly. Every thought about him trying to fight for dominance went out the window. He slumped into submission and let Dean do whatever he desired.

“That’s more like it.”

Dean smirked against Castiel’s skin and grabbed the lube from the nightstand. 

“This is my first time.”

Castiel’s words were a bit slurred by just thinking about it. He was always the dominant one. The one always in control. It felt nice for someone else to take that role and care for him. Within seconds, Dean is pushing his index finger in while Castiel was distracted. One finger prepping his tight hole was already making Castiel moan loudly. Dean clamps a hand on his mouth to keep him quiet as he continues to prep him until he’s nice and open.

“I’ll make it good for you but you have to be quiet, sweetheart.”

Dean removed his hand to get an answer. Castiel was so lost in his pleasure he didn’t comprehend what he called the older man.

“Okay, daddy.”

The name coming from those pretty lips went straight to Dean’s cock. He closed his eyes and sucked in a sharp breath.

“Good boy.”

He patted Castiel’s jaw lovingly and rubbed his thumb against his lip ring. He always admired the boy’s piercings and tattoos. So young but beautiful. Once Dean started to push in, Castiel gasped quietly and bit down on his lower lip to keep himself quiet. His cheeks were flushed and his fingernails started to dig into the palms of his hands. The older man started to rock into him and mark him up with dark hickeys. He also licked over the tattoos he can reach.

“Mine.”

Dean growled and started to pound into Castiel’s tight ass until the boy became a whimpering mess.

“Yours yours yours. Please daddy. Harder.”

The only words Castiel could say at this point. He didn’t bother being quiet anymore. His moans were silence by the headboard banging against the wall as Dean kept thrusting into him.

“Yes, daddy!”

Castiel screamed out when he came all over his stomach. Dean wasn’t much far behind. He came inside the boy and Castiel shivered at the feeling of being marked inside out. He sighed in content when he was released from his bounds. Dean rubbed his wrists before climbing under the covers with Castiel. He wrapped his arms around the boy and pulled him closer. After the mind-blowing sex, Castiel felt guilty. He had cheated on Samandriel because of his own desires.

“You’re okay, Cas.”

Dean whispered and kissed his forehead.

“I know my own son better than you. Surprise. How should I put this? You were his experiment.”

Castiel furrowed his eyebrows in confusion. Not really trying to get what Dean is trying to tell him.

“What do you mean?” 

“I mean, he wanted to experience being with a boy, so he chose you. I didn’t know until recently. That’s why I decided to fuck you today.” 

Dean chuckled and pecked Castiel on the lips. The boy still looked confused though.

“I’ll explain more in the morning. For now, rest. I’ll take care of Samandriel if he throws a tantrum.”

Dean ran his fingers through Castiel’s hair. The boy sighed quietly and closed his eyes. Whatever happens, he knew the older man will be there for him.


	7. Always the Witches

**Summary for the Chapter:**

> When Dean turns down a woman, she curses him.

**Notes for the Chapter:**

> Day 7 of Kinktober - Body Swap

Dean turned over on his bed and burrowed more into the soft cushion. He sighed softly then wrinkled his nose when he breathed in a strong scent of his cologne. Why did his pillow smell so much of it? Did it spill? With that thought in mind, Dean woke up from his deep sleep. He yawned and rubbed the sleep out of his eyes. He lowered his hands and spotted the bee plushie he stuffed his face on. He looked around the room and tried to figure out how he ended up in Castiel’s room. Most importantly, where was the newly human?

He stood up from the bed and left the room. He looked around the hallway and sighed when the others were still asleep. He walked into the bathroom and stopped short when he looked into the mirror. The person looking back at him was not him.

“Cas?”

Dean’s voice sounded a lot like Castiel’s. He looked down at his body and noticed he was wearing pink pajamas with little animals on them. Definitely Castiel’s. Ever since he had turned human he didn’t care about the clothing and chose whatever made him comfortable. The pajamas were comfortable, he had to admit. That’s beside the point. Why was he in Castiel’s body? In addition to that, he really needs to pee.

“I’m going to regret this.”

Dean told himself and sighed miserably. This isn’t how he wanted to see Castiel naked. Of course, the hunter thought about him in explicit ways. Immediately, he regretted it when he felt slick running down the back of his thighs.

“Right, Cas is an omega.”

Dean groaned and shoved his pants down. He cleaned himself quickly before doing his morning business. Castiel’s hands were so small with manicured nails. It was almost adorable if Dean wasn’t trapped inside his body. He took a peek at his cock a couple of times during the morning. It was an impressive size for an omega. Small, but truly perfect. He pulled his pants up and exited the bathroom before he could wet himself again with his fantasies.

While he was thinking about his fantasies, he didn’t notice Sam had woken up already. The door to his bedroom was open and Dean sighed in relief as he dashed into the main room. Sam had a book out in front of him and was enjoying a sandwich filled with so many vegetables. Dean wanted to puke.

“Sam!”

The younger Winchester jumped in surprised and looked over at Dean in alarmed. 

“Oh, good morning Cas. Nice pajamas.” 

Sam bit his lower lip to keep from laughing. Dean narrowed his eyes as he thought about how long Sam would be knocked out if he punched him right now. The sudden protectiveness surprised Dean. He thought these pajamas were ridiculous too, but Sam having the same opinion irked Dean.

“It’s me, Dean. I’m stuck in Cas’ body!”

Dean gestured toward the foreign body and widened his eyes. Sam chewed slowly on his sandwich as he looked at Dean up and down. 

“Are you listening to me, moose?!”

Dean huffed. Sam finally swallowed his bite and nodded.

“Yeah, that’s definitely you. Cas doesn’t call me that.”

He stood up from his chair and walked towards Dean. The older Winchester had to tilt his head back to look up at him. Sam has a smug look on his face at how short Dean was. So this is how Castiel feels like when dealing with the alpha brothers being so tall.

“Haha. I’m short whatever. Fix this!”

Dean stomped Sam’s foot who winced and nodded quickly.

“Okay okay. Where’s Cas anyways?” 

Speak of the devil, Castiel came into the room in Dean’s body. He was wearing a gray robe to cover his body.

“I think there’s a problem.”

Castiel said in a monotone voice. Definitely him, Sam thought.

“What happened last night? Think.”

Sam commanded and stood in between the two. Castiel tilted his head to the side and squinted. Dean crossed his arms and thought about it.

“I was watching TV. That’s it.” 

“I went out to a bar and turned down the bartender.”

Sam sighed and nodded.

“So it’s probably the bartender. I’ll go investigate while you two stay here. Text me what bar, Dean.”

Sam grabbed the keys to the Impala and ignored Dean’s protest when he was out the door already. The older Winchester groaned and walked towards Castiel to feel his pockets for his phone. He texted Sam the address and placed it back inside the pocket. 

“He better hurry up. I don’t like it when fluids are coming out of my ass.”

“If you’re complaining about that then I shall too. How do you control this knot? When I woke up it was enormous.”

Castiel looked down and poked at the bulge. Dean threw his head back and burst out laughing. Castiel looked confused but smile anyway. He felt accomplished for making the hunter laugh even though he didn’t know what about.

  * \-     -



When Sam came back from the bar he stepped in a middle of Dean and Castiel bickering.

“Whoa whoa whoa. What’s going on?”

He asked as he tossed the keys on the table. Dean waved his arms towards Castiel’s body.

“Look at him! What is this?!”

Castiel decided to change into clothes and wore one of Dean’s Led Zeppelin shirts. He tucked the shirt into Dean’s jeans and wore a belt. He also slicked his hair back to look nice. Meanwhile, Dean was wearing a flannel that looked way too big on Castiel’s frame and baggy jeans. Sam almost wanted to smack the both of them.

“I’m going to make this quick before you two actually fight over clothing. I talked to the bartender, and turns out she’s a witch. She was trying to help you, Dean.” 

Dean raised his eyebrows and opened his mouth to object, but Sam waved him off.

“Because you two are oblivious people who keep dancing around each other! I’m sick and tired of the sexual intention in the room. That’s beside the point; if you two knuckleheads kiss you’ll return to your rightful bodies. Do you want to know why? It’s because you love each other. Surprise. Surprise. Now, I’m going to grab another car and leave because I don’t want your alpha ass beating the shit out of me. Be as loud as you want!”

Sam was breathing heavily once he finished his speech and left the room as quickly as possible. He didn’t want to be in the middle of a makeout session or worse. Castiel was fiddling with his fingers and made himself small despite Dean having a large frame. His cheeks were heating up in embarrassment. So that’s how Dean looked when he blushes. It’s true when people say his freckles pop out. 

“We’re a couple of dumbasses huh?”

Dean spoke up to break the tense atmosphere in the room. Castiel looked up at Dean.

“I prefer the term...scared. Less dumb. Less ass.”

Dean smiled at what Castiel said and nodded in agreement. They both were scared. Scared to lose each other. 

“I prefer that too.”

Castiel smiled and looked away from Dean. It seemed like he wasn’t going to make the first move. Always the shy one. Dean sighed and took the matter into his own hands. He would rather be in his own body. He walked up to Castiel and grabbed his face to pull him down and kiss him. He felt Castiel tensed up but immediately relaxed and started to kiss back. Once Dean pulled away he was looking into those baby blue eyes he loved so much.

“There you are.”

Dean whispered and leaned in to kiss him again. Castiel melted into his grasp and sighed happily. He was like a lovestruck fool when he looked up at Dean with such trust and love in his eyes. At that moment, Dean wanted more. He picked Castiel’s up from the floor. The omega’s surprised squeaked was muffled by Dean’s lips as they stumbled into his room. He pinned the omega to the bed and growled softly when Castiel slump in submission.

“Good, omega.”

Dean huffed when he tried to take off his shirt from his pants. He tossed it aside in frustration.

“You look nice when you have your shirt tucked in.” 

Castiel said truthfully when he started to unbutton his flannel.

“Next time, no flannels. It’s time consuming when I try to unbutton them.”

Dean nodded in agreement as he pulled the flannel away. He took off their pants and moaned quietly when Castiel ran a hand through his gelled hair.

“You look quite handsome.”

Castiel smirked, but it faded away when Dean stuffed two fingers inside of him. He groaned loudly and clenched around them. A great way to wipe off that smirk out of his face. Dean’s fingers were way better than his own small ones.

“And you look sexy, baby.”

Dean growled and prepped Castiel quickly. The omega just had his heat which meant he was stretched out just perfectly. It took every ounce of willpower to refrain himself from kicking down Castiel’s door to take him those few days. Now that he gets to take him, Dean wants to make this wonderful for him.

“Hurry, Dean. I’m not fragile. I want that big cock inside me.”

Those filthy words coming out of Castiel’s pretty pink lips were like music to Dean’s ears. He pulled his fingers out that was covered in slick. He stroked his cock and squeezed the head to keep from coming. Castiel turned onto his stomach and lifted himself up to his hands and knees. He looked over his shoulder and moaned loudly when Dean pushed into him without warning. His arms gave out in front of him when Dean set a rough pace. The alpha wasn’t in control of his instincts anymore and Castiel could only just stay there and take the brutal pounding. He gripped the sheets beneath him as moans were spilling out of his mouth. 

“That’s it, my pretty little omega.”

Dean groaned. He gripped Castiel’s hair and pinned his head to the mattress as he felt his knot swell until it started to tug on the omega’s rim. He teased it against the muscle and chuckled when the omega pushed back in frustration.

“Stop playing with me, Dean!” 

Castiel whimpered. He couldn’t move his hips that far with Dean pinning him down. All he could do was beg until the alpha gave it to him, and he did. Dean thrust his knot inside Castiel and came inside him with a shout. He leaned down and bit down on the omega’s shoulder. Castiel screamed out his pleasure and slumped into a pool of his own cum. He wrinkled his nose and groaned quietly when Dean turned them onto their sides. Castiel yawned from the intense fucking they just did and closed his eyes.

“Hey, Cas?”

“Yes, Dean?”

“Why does your bee smell like my cologne?”

Castiel’s eyes snapped open, and he looked over his shoulder at Dean. His whole face was red from the sex and being embarrassed. He looked everywhere except Dean.

“Your scent helps me sleep at night. Of course, I can’t get your natural scent, so that’s why I stole your cologne.”

Castiel burrowed into the pillow to hide his face. He breathed in and sighed when the pillow smelt just like Dean. 

“Now that we’re together, you can smell me whenever you want.”

Dean laughed and poked Castiel on the arm who slapped his hand away. Adorable.

“Thank you, Dean.”

Castiel’s response was muffled but Dean still heard it. He smiled and kissed the omega’s forehead.

“You’re welcome, Cas.”


	8. Awfully Perfect

**Summary for the Chapter:**

> Dean kills his victim before Castiel comes home.

**Notes for the Chapter:**

> Day 8 of Kinktober - Blood/Gore

****Dean dragged the chair Metatron was tied to in the middle of the room. The man struggled against his bonds as Dean looked at the torturing materials on the tray. He had a wicked grin on his face as his fingertips touched the utensils. So many possibilities to kill this man in so little time. Castiel would be home any minute now, so Dean had to make this quick. He knew the man didn’t like waiting. One of the many reasons why he loves him so much. He could get so feisty and all riled up when Dean took his sweet as time. Today, Dean was in the mood for sex, so he wouldn’t disappoint Castiel and make him wait.

“How should I kill you? I would love to torture you, but I don’t have much time.”

Dean pouted at the idea. The next victim Castiel promised him he would be able to torture them. He loved it when the man kept his promises. Castiel was just in the mood for some hard fucking after his normal day at work. Dean couldn’t blame him. Working to try and be normal, sucked. 

“Please! Don’t kill me!”

Metatron cried out as he struggled even more against the chair. Dean laughed loudly and shook his head. 

“Beg all you want, you’re never getting out of this place.”

Dean hummed as he grabbed a scalpel. He could already hear Castiel nagging when he comes home to find that the victim is still alive. He puts the tool down and settles for a sharp knife.

“Lucky for you, I’ll make this quick. My husband doesn’t like waiting.” 

He looked down at the silver band on his ring finger and smiled happily. Metatron didn’t seem to hear since he was screaming for help. Pathetic. They were in the woods. Many miles away from any human being. He wielded his knife and struck Metatron’s chest. The man howled in pain as Dean kept digging the edge of his blade into his flesh. He used his bare hands to break open his rib cage. He relished on the screams Metatron was making until he ripped his still beating heart.

The man’s corpse slumped and the heart stopped beating. Dean was covered in blood, and he loved it. He closed his eyes and breathed in the scent of blood. He always enjoyed that scent. The scent of the guilty being brutally murdered by Dean’s own bare hands. It was exquisite. He was so out of it he didn’t hear the door open until he felt a new presence. He snapped his eyes open and glanced over at Castiel. His pupils were blown wide from lust which made Castiel smirked.

“Did you have fun, dear?”

Castiel asked as he walked closer to Dean who nodded eagerly. He placed the heart down on the tray and grabbed Castiel’s face to kiss him hungrily. He pulled his husband towards his chest and covered him in the victim’s blood. Castiel moaned and rolled his hips against Dean. He was happy to find out that his husband was sporting a hard-on already. 

“You know me. I always do, baby.” 

Dean rasped darkly as he looked into those murderous blue eyes. Those eyes he fell in love with the first time he saw them. He truly made a perfect choice.

“I want you now.” 

Castiel whined as he started to shed off his clothes. Dean followed suit and backed Castiel until the tray dug into the small of his back. Dean growled in frustration and pinned Castiel to the ground. He didn’t have the patience to head to their bedroom. No patience to grab the bottle of lube or some condoms. He slipped his hand in between Castiel’s open thighs and rubbed his rim with the victim’s blood. It was still wet when he slipped his finger inside his husband.

“Oh fuck. That feels good.”

Castiel dropped his head against the floor and moaned quietly. They’ve done this before whenever Dean didn’t have the patience for anything else. He just wanted to be inside his husband _now._ Castiel loved how kinky he can get. It just made him even harder. He wrapped his legs around Dean’s waist and pushed back against the finger until Dean slipped in another one. 

“This is so much better than torturing.”

Dean declared. He prepped Castiel quickly and took out his fingers. His husband loved the pain so he pushed inside him without coating his cock. He moaned loudly and didn’t wait for Castiel to get used to his length. He started to pound into him and pinned Castiel’s wrists above his head.

“Scream for me, baby. Your screams are my favorite.”

Dean licked his lips and expressed his statements when he rammed Castiel’s prostate. Castiel couldn’t do anything but obey. He screamed out his pleasure and kept pushing back against Dean’s cock. The skin slapping against skin and Castiel’s screams were the only sounds in the room. Truly perfect. 

“Come on, baby. Cum for me.”

Dean leaned down and bit Castiel’s shoulder so hard he broke the skin. The taste of copper when Castiel’s blood flooded his mouth made him moan. That was the last straw for Castiel. He came all over his stomach with a whimper and thrashed against Dean. 

“Oh, Dean!”

Dean grinned wickedly as he licked over the wound. It was going to leave another scar. A new collection to the many scars Castiel has because of him. 

“Mine.”

Dean thrust in a couple of times and came inside Castiel, marking him all over again. He crashed their lips together and kissed all over Castiel’s face. Some blood dropped out of his mouth and onto Castiel’s face, but he didn’t care. 

“I love you, Cas.”

“I love you too, Dean.”

“Who’s our next victim?”

Dean asked after a while and pulled away from Castiel’s neck to look down at his husband. The man thought about it as he went over the list in his mind. 

“This time you’ll choose.” 

Dean grinned at the idea and nodded. This was going to be fun.


	9. Surprises are the Best

**Summary for the Chapter:**

> Castiel decides to surprise Dean by baking him a pie and wearing lingerie.

**Notes for the Chapter:**

> Day 9 of Kinktober - Lingerie

Castiel cooed softly as he rocked his pup to try and get him to sleep. Jack snuggled into his chest and sighed softly. He fiddled with a thread on his papa’s shirt and felt his eyelids droop slightly from exhaustion.

“Papa, I don’t want to sleep.”

Jack pouted up at Castiel. He made his puppy dog eyes he got from his omega father, but they didn’t work on Castiel this time. He shook his head and squeezed Jack’s chubby cheeks. 

“Not today, little one. You have your first day of school tomorrow. Maybe on Friday, you can stay up if you behave during the week. Deal?”

Castiel raised his eyebrows as Jack thought about it. Finally, he nodded excitedly and smiled. 

“Deal!”

Castiel nuzzled Jack and breathed in his scent. His pup’s and mate’s scents always calmed him. He didn’t know what he’ll do without them. He rocked the chair back and forth until Jack was asleep. He stood up from the rocking chair and walked towards Jack’s bedroom. He placed the five-year-old pup on his bed and covered him with the comfy blankets. 

“Good night, Jack. Sweet dreams.”

Castiel kissed his forehead and smiled when he pulled away. He turned off the light and closed the door behind him. Now that his pup was asleep he felt excited. Dean would come home soon which meant Castiel didn’t have a lot of time to prepare this evening. He needed to get started quickly. Thankfully, Jack fell asleep right on time. Ever since his alpha took that job Dean was building up stress over time. Of course, he always hid it, but Castiel knew his mate well. He also knew how to relieve all that stress. He walked towards the kitchen and searched through all the cabinets for the equipment he needed for an apple pie. Dean’s favorite.

He hummed a tune as he made the pie. About an hour the oven dinged indicating the pie was done. He slipped on some oven mitts and took out the pan. While the pie was baking he cleaned the kitchen quickly. He closed his eyes and breathed in deeply. Delicious. He sets it on a cooling rack and returns the oven mitts to their rightful drawer. 

“All done. Now, for the outfit.”

Castiel grinned wickedly as he skipped towards the master bedroom. He tapped his chin as he looked at all the various types of clothing in his closet. 

“What should I wear?”

He thought for a bit until he gasped. He crouched by the bed and pulled out a box. He opened the black box and pulled out the black three-piece babydoll lingerie set. He decided to treat himself and bought this with his own money. Dean kept buying him new things ever since he made his own business. The alpha was going to freak when he saw this on Castiel. It made the omega giggle and smile to himself. He strips out of his clothes and puts on the babydoll. He stuffs the box under the bed and stands up from the ground to grab a robe from the closet.

He looks himself in the mirror and twirls around to see the whole outfit that revealed so much skin. When he heard the front door open he slips on the pink robe and ties it around his waist. He took a couple of deep breaths to calm himself down. Doubts were coming into mind, but he ignored them. Dean will love this. With that thought in mind, he walked towards the living room. Dean slipped out of his suit jacket and hung it on the wall. He smiled when he saw his mate and engulfed him into a hug. Castiel wrapped his arms around the alpha’s neck and hugged him tightly. 

“Hey, baby. I missed you.”

Dean said and pulled away to peck Castiel on the lips. He stops short and scented the air. He narrowed his eyes toward the direction of the kitchen and grinned.

“You made pie?”

Castiel nodded and grabbed Dean’s hand to lead him into the kitchen. The alpha kept breathing in the scent until he spotted the pie. He licked his lips and grabbed a plate from the cabinets to cut himself a piece. He grabbed a fork and sat down by the dining table to start eating it. 

“This is so good, baby.”

Dean moaned as he wolfed down the piece of the pie. Castiel giggled and handed Dean the whole pie. 

“All of it is for you, sweetie. I made it just for you. I know how big your appetite can be especially after a long day at work.”

Castiel patted Dean’s belly and giggled again when the alpha growled playfully at him. Dean grinned and kissed Castiel’s cheek and started on another piece. He even shared the pie and fed Castiel a couple of small pieces. It was a damn good pie, Castiel had to admit. The couple finished the pie and the omega put the dirty dishes in the sink to wash tomorrow. 

“I’m tired.”

Dean yawned as he stood up from the seat and grabbed Castiel’s hand to guide him to their bedroom. The omega bit his lip and hoped that Dean wasn’t too tired. He was thinking about this night all day. When they entered the room Castiel locked the door behind him and stayed by the doorway as he watched Dean stripped the rest of his clothes off. The alpha felt his gaze and turned towards Castiel with a confused expression. 

“Are you going to join me?”

Dean asked. Castiel let out a shaky breath and nodded slowly. Well, now or never. He untied the pink robe and let it pool onto the floor. The alpha’s eyes widened in surprise, and he reacted quickly. He backed the small omega against the door until there wasn’t any space in between them. Dean growled and crouched in front of Castiel. His hands roamed all over the omega’s body. Paying close attention to the more sensitive spots Castiel had. The omega had to bite his lip to keep from moaning too loud.

“So beautiful.”

Dean’s praise made Castiel’s cheeks heat up. He smiled and ran his fingers through Dean’s hair. The alpha turned Castiel around and immediately pulled his panties down. He kneaded the omega’s ass cheeks and spread them. Castiel’s face turned red, and he tried to shy away from Dean but he had a tight grip on him. The alpha stuffed his face in between his ass cheeks and started to lick his hole.

“Oh!” 

Castiel clamped a hand over his mouth and pushed back against Dean’s face. The alpha drank up all the slick his mate had to offer. Some of it fell down his chin but he was too out of it to notice. He swirled his tongue around the rim and prodded it until his tongue breached the tight ring of muscle. He added his index finger along with his tongue.

“Mmm Dean. That feels so good, alpha.”

Castiel gasped quietly as he grabbed a handful of Dean’s hair and scratched the door just slightly. His legs started to shake from trying to hold himself up. He didn’t think he was going to last long. They hadn’t had sex in a long time and Castiel felt like a virgin. The thought made him blush. He knew Dean’s stamina could go on for hours if he wanted to, but Castiel needed to take Jack to the school tomorrow. Maybe another time. So many ideas were popping up in Castiel’s head on how he can seduce his alpha.

“Yes!”

Castiel jumped when Dean found his prostate. Slurps and the squelch of the alpha’s fingers were the only loud noises in the bedroom while Castiel tried to hold in his moans. He was shaking and felt pre-cum wet the front of his panties. 

“You’re going to cum for me, baby?”

Dean rasped against Castiel’s skin. The vibrations of his voice and his stubble rubbing against his ass made the omega shiver.

“Yes, alpha.” 

Castiel panted and let out a silent scream when Dean rubbed against his prostate until he came in his panties. His knees buckled, and he was saved from Dean who stood up quickly to catch him before he could fall. The alpha carried him to the bed and prepped kisses all over his face.

“Thank you, Cas. I needed this.”

Dean whispered as he helped Castiel out of the babydoll. He smiled at his mate and pulled him in for a passionate kiss. 

“You’re welcome, Dean. It’s what you deserve.”

Castiel said honestly and yawned. He smacked his lips and nuzzled Dean. The alpha squeezed his mate tightly and had a permanent smile on his face for the rest of the night.


	10. Homework is Important

**Summary for the Chapter:**

> Dean suggests a break when Castiel is doing homework.

**Notes for the Chapter:**

> Day 10 of Kinktober - Hair-pulling

Castiel laid on his stomach and propped himself up with his elbows as he typed his essay on a laptop. He barely had one paragraph done. He blew the piece of hair out of his face as he looked down at the worksheet that had the requirements listed down. 

“What did you write for the second paragraph?”

Castiel asked Dean who was laying on the bed next to him. He was on his back and looked over his phone at his boyfriend. 

“I haven’t even started.”

Dean said which made Castiel roll his eyes. Of course, he didn’t do it. When did Dean ever do his homework?

“I’m trying to help you pass your classes, Dean. I can’t do that if you don’t put in any effort.”

He sighed and glared at Dean over his shoulder. The boy merely grinned mischievously. Why did he have to be so hot? He was Castiel’s weakness and could never be angry at that face.

“Sorry, babe. Homework is just boring for me. I can’t concentrate.”

Dean shrugged as he shut off his phone and tossed it aside. He put his hands behind his head and leaned back against the pillow with a sigh. Castiel saw the muscles Dean was showing off and bit his lip. He looked back at the screen and huffed. He didn’t need any distractions. Especially when those distractions involve Dean Winchester showing off what Castiel likes.

“You need to take a break, babes, and I know just the perfect solution.”

Suddenly, Castiel felt hot breath against the back of his neck as Dean loomed over him. He felt his boyfriend prep kisses all over his neck and giggled as he shoved Dean’s face away.

“Dean! I’m doing homework.”

Castiel snapped and tried to bat Dean away when he tried to kiss him. The boy catches his wrist with a threatening growl and continues to kiss all over his neck. Castiel ignores him and tries to tug his hand away to continue with his essay. Dean pushes a hand into his hair and pulls his head back.

“Don’t be like that, sweetheart. You belong to me, and I’ll do as I please.”

He shut the laptop and placed it on the nightstand. He wasn’t stupid to just leave it there. Castiel wouldn’t forgive him for accidentally break it. He stuffed Castiel’s face into the sheets and covers his body with Dean’s. The boy was already panting and blushing from being pinned down. He rolled his hips against the bed for friction and bit his lip.

“Get on with it then, Dean. Your mom will be home soon.”

Castiel chuckled when he heard Dean made a noise of disgust. He always brought up unnecessary topics to ruin the mood. This time, it didn’t work. Dean was already sporting a hard-on and rubbing against the crack of Castiel’s ass. The boy moaned quietly and gripped the sheets. He shivered and squeezed his eyes shut. He felt heat pull in the pit of his stomach as Dean’s breathing started to pick up.

“Please, Dean.”

Castiel begged quietly and sighed when Dean pulled away slightly to remove his sweatpants. They both decided to go commando since Dean couldn’t control his libido. He felt the head of Dean’s cock nudge against his hole and jumped slightly. The grip on his hair loosened and he was able to breathe in enough air.

“Dean! The lube is in my drawer.”

He squeaked out and felt Dean’s weight on him disappear. The boy searched through the drawers next to the bed until he found the bottle of lube. He wasted no time in returning to his previous position. He drizzled lube onto Castiel’s hole and stuffed two fingers inside him. The boy arched his back and pushed back against Dean’s fingers.

“You’re such a slut for this.”

Dean hummed and gripped Castiel’s hair again. He pulled back, and the boy hissed in pain. He welcomed it and moaned so prettily Dean could just cum from those sounds. 

“Please, Dean! I need it.” 

Castiel whimpered when Dean pulled his fingers out. He felt empty and in pain as the grip on his hair increased when Dean moved away to coat his cock.

“I got you, baby. Just let me take care of you.” 

Dean nudged his cock against Castiel’s hole and pushed in. He pinned Castiel’s head down again and rammed inside him. The boy’s shouts and moans were muffled with the sheets as Dean pound into him. All he could manage to say was Dean’s name and plead for more. The boy gave it to him and felt himself already getting close.

“Yes, Dean!”

Castiel came all over the sheets and his thighs quivered as Dean followed suit. The boy groaned and wrapped his arms around Castiel to pull him onto his lap. Castiel moaned quietly and gripped Dean’s biceps. He felt full with Dean’s soft cock inside him and smiled.

“Now I won’t be able to finish the essay!”

Castiel pouted and slapped Dean’s chest who laughed. The boy surged forward to kiss his boyfriend.


	11. Anything Else, Mr. Winchester?

**Summary for the Chapter:**

> Castiel decides to wear a skirt instead of a suit for work.

**Notes for the Chapter:**

> Day 11 of Kinktober - Cross-dressing

The sunlight shining through the curtains made Castiel groan. He pulled the blanket over his head to block it out, and a few minutes later his alarm rang. He groaned even louder and threw the blanket off. He stood up from the bed and caught himself by placing a hand on the wall for standing up too fast. If he didn’t get up right away he would sleep for another ten minutes. He rubbed his eyes and glanced at the chair where he placed his clothes at. Just by looking at them made Castiel nervous. His heartbeat picked up by just imagining himself walking through those double doors in that outfit. He was able to lay off his choice of clothing so far but felt uncomfortable in his suits.

He walked towards the pile of clothing and started to change into them. He would not back out from this. He felt pretty and comfortable in this outfit. He just hoped nobody would be making crude comments about it. He looked at himself in the mirror and smiled. His white dress shirt was tucked into his black skirt that fit perfectly and showed off his curves. He tied his tie and slipped on some thigh highs along with his flats. Those tight dress shoes made his small toe ache, and he was glad to wear the flats that actually fit him. He sang quietly as he waltzes into the bathroom to fix his hair, he could never fix it, and brush his teeth.

Once he was done, he walked into the kitchen and looked through the refrigerator for the leftover salad. His boss always loved this kind of salad and Castiel decided to try it himself. He wasn’t disappointed. He opened the salad and grabbed a fork to start eating it. Once his stomach was full and the plastic bowl was empty he cleaned himself up before grabbing his bag to leave the apartment. He smiled on his way to his workspace. He was smart enough to rent the apartment closest to the company since he still couldn’t afford a car. He barely started this job and already loved it.

He pushed the door open and greeted his friend Meg at the front desk. “Good morning, Meg. It’s nice to see you.” He said with a grin.

His friend quirked an eyebrow then smirked when she noticed his outfit. “Nice outfit, Clarence! I love to see more of that.” She gave him a thumbs up when the man pressed the button for the elevator.

The compliment made him blush, and he thanked her as he walked back into the elevator. He raised onto his tippy toes and landed back on his heels and continued the motion until the elevator reached the floor he needed to be at. He stepped out of the elevator and walked towards his desk that was in front of his boss’s office. He placed his bag down and bent against the desk to look at the papers someone placed on the wooded area.

  * \-     -



Dean was on his phone when the elevator doors opened. He stepped out, along with other people he ignored, and automatically headed towards his office. He shut his phone off and looked up. He stopped in his tracks when a woman was bent over his secretary's desk. He licked his lips when his eyes roamed her curvy body. When the person turned to look at him he almost choked on his own saliva. Castiel’s brows furrowed in concern at Dean’s horrified expression. Right. That wasn’t an appropriate expression based on what his secretary is wearing for the first time. He looks so good in that pretty skirt. Much better than those monkey suits the man looks uncomfortable in. He didn’t think he was able to form any words until Castiel spoke up in a quiet voice.

“Are you alright, Mr. Winchester?” Castiel asked gently as he rubbed his arm awkwardly.

“Yeah, yeah. You look good. I mean...I’m good.” Dean cleared his throat and smiled sheepishly as he shuffled towards his office before he could embarrass himself even more. He didn’t notice the smile that formed on Castiel’s face.

When Dean shut the door behind him he felt like he could breathe now. He placed his suitcase on the desk and plopped down on the leather chair. He glared down at his hard-on and poked it. His sexual and romantic feelings for Castiel were growing stronger by the day, and it didn’t help that the man was wearing a _skirt._ Life just really hated Dean right now. He sighed as he rubbed his eyes. His fingers twitched when he stared at the phone. It taunted him. Daring him to pick it up and _call._

He turned away and opened his suitcase to take out the papers and start on them. He uncapped his pen and stared at the paper and wished the form could just write itself. He spends a few minutes just staring at it until his nagging thought won the battle. Before he could stop himself, he picked up the phone and dialed a number he knew by memory. The phone rang until Castiel picked up.

“Hello?”

“Hey. Sorry to bother you but I forgot to make my coffee this morning. I can’t concentrate until I take my daily dose of caffeine.” Dean leaned back against his chair and felt his heart racing when he heard a slight chuckle from Castiel that turned into a cough. It made him smirk. He knew what Castiel did. At least he was able to make him laugh.

“Yes, sir. I’ll get on it right away.”

“Thanks. I appreciate it.” Dean hung up the phone and let out a breath he didn’t know he was holding. It was true he didn’t get his coffee only because he didn’t want any today, but damn, he wanted to see Castiel in that skirt more closely.

Dean finally wrote something down when he heard his door open. He looked up and placed his pen down when Castiel came into the room shyly. He smiled and placed the cup of coffee on Dean’s desk.

“Anything else, Mr. Winchester?” Castiel asked sweetly.

“Well, you can get on your knees,” Dean said under his breath as he grabbed the coffee to sip on it.

Castiel flushed at the comment he wasn’t even supposed to hear but didn’t look uncomfortable by it. “Yes, sir” he purred. He got a boost of confidence when Dean looked up in shock. He batted his eyes at his boss as he lowered himself onto his knees. He was so close Dean almost ached for it. His cock twitched in interest as Castiel rubbed his thighs, but before they could get anything done or say anything the phone rings. Dean almost huffs in disappointment when Castiel stands up to answer the phone.

“Mr. Winchester’s secretary speaking. How may I help?” Castiel greets the caller and sits down on Dean’s lap. He felt the man’s hands on his hips and smirked when he grounded down against his hard cock. His boss made a small noise and his grip tightened.

“Naughty” Dean chuckled harshly as he thrust up against the crack of Castiel’s ass. The man leaned his head back against Dean’s shoulder and hummed happily. Dean could hear a muffled voice on the call and hoped Castiel hung up soon.

He stood up from the chair and pinned Castiel to the desk. He bent him down and ignored Castiel talking on the phone as he pushed his skirt down. He rubbed his hole with a dry finger, and Castiel gasped softly. “I-I’m sorry. J-just sick.” Castiel cleared his throat and unbuttoned the first button on his dress shirt.

Dean rolled his eyes and pried the phone from Castiel’s hand. He hung up and turned his head to capture the man’s lips. Castiel sighed softly and kissed back just as eagerly. “The call can wait” Dean growled softly as he fumbled to unbuckle his belt and shove his dress pants down. “You’re so hot, baby.”

“Mmm. I’ve wanted this for so long.” Castiel admitted and bit his lip seductively. He looked up at Dean with his innocent eyes.

“Me too.” Dean licked the shell of Castiel’s ear and reached out to pull a drawer and grab lube. “I’m going to fuck you so hard, Cas.” He growled and kissed his neck. He bit down on Castiel’s neck and licked over the mark with his tongue. The man whimpered quietly and ran a hand through Dean’s hair.

“Please, sir!” Castiel panted and squeaked when Dean slid a finger inside him. He shivered and couldn’t do anything but take what Dean chooses to give him. He loved how plaint the man is. He wished he could have Castiel like this forever. He added another finger and prepped him slowly. Castiel was getting frustrated and could barely stand from how intense his arousal is. “Dean! Please!” He sobbed and rubbed against the desk for friction.

“So impatient.” Dean chuckled darkly when he pulled his fingers out. He licked his lips as he stroked his cock and pushed into the smaller man. He looked down where they were joined and circled his hips. He watched himself fucking into Castiel and groaned at the sight. The man was helpless against Dean’s grip. He loved it.

“Yes! That feels so much better.” Castiel sighed happily and closed his eyes to bask in the moment. Feeling so full. Meanwhile, Dean could barely control himself because of the tight heat surrounding his cock. He could barely remember when was the last time he had sex like this. Maybe never since Castiel was so special.

“Mmm baby.” Dean groaned as he thrust in roughly. He gripped Castiel’s hips and slammed into him. Castiel had to grip the edge of the desk and couldn’t contain his moans. It just felt so good. The chance of them being caught just added to the thrill.

“Right there!” Castiel’s legs shook when the head of Dean’s cock rammed his prostate. He came all over the desk with a shout and could barely keep himself up. Dean wrapped his arms around Castiel and sat down on the leather chair. The man whined quietly when Dean’s still hard cock nudged his prostate.

“I’m going to keep you here while I finish this paperwork, and once I’m done I’m going to fuck you again.” Dean’s deep voice sent shivers down Castiel’s spine. He nodded obediently and smiled to himself. He loves his job.


	12. Naughty Bunny

**Summary for the Chapter:**

> This Halloween, Dean decided to dress up as a cop and Castiel a sexy bunny.

**Notes for the Chapter:**

> Day 12 of Kinktober - Costumes

Dean was excited for today. Today was Halloween and had an excuse to go trick or treating with his boyfriend and little brother. Apparently, he was “too old” to get candy as the neighbors so kindly put it. He didn’t care. He wanted to drive to the rich neighborhood and get his bag filled up with king sized candy bars.

He had his police costume on and had a plastic bag for the candy. He grabbed his keys from the bowl, that was next to the front door, and left the house. He climbed into the driver’s seat and drove towards Castiel’s house. He wondered what Castiel was going to wear. His boyfriend didn’t give him any hints, and Dean was curious. When he got there he grabbed his phone to shoot Castiel a text message. A couple of minutes later his boyfriend walked outside along with his little brother Samandriel. The kid was wearing a cute dinosaur costume while Castiel was wearing a sexy bunny costume. He looked delicious. Especially with those fishnets, he has on. Dean licked his lips and felt his cock hardened. He took a couple of deep breaths to calm himself down because they weren’t alone.

“Hello, Dean” Castiel greeted him when he slipped into the passenger’s seat while Samandriel hopped onto the backseat. “Ready to go?” He smirked and leaned back against the seat to show off his legs. What a naughty bunny.

Dean cleared his throat and nodded. “Yeah. Let’s go.” He looked up ahead as he backed out of the driveway. He kept trying to glance over at Castiel and his outfit. It covered nothing to the imagination.

The long tortuous ride ended when they arrived at their destination. Dean looked around for parking until he found a spot his impala would fit. He parked the car, and the three of them climbed out with their empty bags ready to be filled with lots of candy. Dean looked around and considered which way to go. “Looks like the left has more houses giving out candy.” He pointed his thumb towards the left and gestured to the other two to follow him.

Castiel slid up next to Dean and nudged his shoulder with a shy smile. “Do you like my costume?” He purred.

Dean gulped and nodded just slightly. He had to remind himself that there were kids around but dammit, Castiel looked so pretty. “I love it. It’s not fair you’re trying to tease me while we’re trick or treating.” He glared over at his boyfriend who giggled softly. He skipped along the pathway with his little brother and they walked up to the first house. Dean and Castiel held out their bags and grinned at the man who quirked an eyebrow. The man shrugged and gave candy them candy as well. They walked around the neighborhood for about an hour. Castiel started to shiver from how much the temperature dropped. Maybe it wasn’t such a good idea to wear this costume after all. Dean chuckled softly and took off his jacket. He helped Castiel slip it on and kissed his cheek.

“Thank you, Dean.” Castiel ducked his head to hide the blush that formed. “I was freezing.”

“It’s no problem. I’m just surprised you held out this long.” Dean winked and looked down at his half-full bag. Another hour and it’ll be filled.

The people always gave Samandriel some extra candy because he was a kid and his costume was very cute. They all loved it. Samandriel’s bag was filled up first and they walked around some more until Dean and Castiel’s bags were also full. They retired back to the Impala and Dean drove them home.

“I had so much fun! I can’t wait to eat all this candy.” Samandriel grinned as he looked through all the candy in his bag. He was going to dump them on his bed and share some with his friends who weren’t able to go trick or treating.

“Me too! I’m going to get some diabetes.” Dean joked with a snicker when Castiel slapped his arm playfully. He has a sweet tooth. What can he do?

“I’ll see you later, Dean!” Samandriel waved at the man before getting out of the car and going inside the house. Once the kid was out of side Castiel scooted closer to Dean and placed a small hand on his thigh.

“Arrest me, Officer” Castiel purred seductively and winked.

Dean moaned at how sexy his boyfriend was and felt his cock hardened. Castiel took off Dean’s jacket and climbed onto Dean’s lap. He kissed him and grounded their clothed cocks together. He gripped the leather seat and whimpered quietly as he kept dry humping Dean. It felt too good to stop. He broke the kiss and dropped his head on Dean’s shoulder as his breathing picked up.

“Mm baby.” Dean groaned as he reached behind Castiel to unzip his costume. They struggled a bit to take it off and Dean nearly ripped the fishnets to get to Castiel’s cock. Once the man was naked and a whimpering mess on his lap Dean reached in between them to unzip his trousers. He took out his cock and wrapped both hands around their cocks.

“That feels so good, fuck.” Castiel chewed on his bottom lip as he thrust up into Dean’s fist. The man stroked their cocks and started to attack Castiel’s neck. He left dark marks behind and growled. His hands started to slick from the pre-cum which gave the two men more friction.

Castiel’s bunny ears fell on the ground as he covered Dean’s hand with his own to help stroke their cocks. He gasped as he started to cum. The strips of cum landed on Dean’s hand but didn’t mind the extra friction. Stroking himself with Castiel’s cum turned Dean on, and he couldn’t help the orgasm that was ripped out of him. He panted as he leaned his head back against the seat. Castiel hummed happily and laid his head on Dean’s chest. Maybe next Halloween he can choose another sexy outfit if their night ends like this again.


	13. Master

**Summary for the Chapter:**

> Castiel waits for his master’s return.

**Notes for the Chapter:**

> Day 13 of Kinktober - Gags

Castiel was tied and laying on the king-sized bed. Muffled whimpers and a buzzing noise can be heard while Castiel was waiting for his master to return. His master had put on a gag on Castiel and left a vibrator inside him; turned on to the highest setting. It was buzzing against his prostate, and he came at least three times while Dean was away. It felt so good. Tears streamed down his puffy face as he sobbed into the gag. He thrashed against the bed and panted heavily. Dean didn’t tell him where he was going, so he couldn’t do anything but stay on the bed. Waiting. He was pretty sure he passed out at least once or twice during the wait. His mind was distant and lost.

He clenched his fingers and tugged on the bonds. Reg rings started to form on his wrists from tugging too hard on the rope. He loved the extra pain that came when his master tied his wrists too tight. He squeezed his eyes shut and his toes curled as he felt himself getting close again.

He was enjoying himself and didn’t hear the door open. He didn’t hear the man coming closer until he felt a hand on his thigh. He jumped and his eyes snapped opened to look up into green eyes full of want. Dean licked his lips when he roamed his eyes on Castiel’s body. His slave was so beautiful and perfect. Full of sweat, tears, and cum. Truly a sight that will be burned into his memory. He sat down in between Castiel’s legs and rubbed his thighs. Castiel whimpered and thrust his hips upwards.

“Needy boy.” Dean hummed softly. He grinned wickedly as he grabbed the vibrator and thrust it in and out of Castiel. He screamed and threw his head back against the pillow. He sobbed as his sensitivity spiked up when Dean kept continuing to thrust the vibrator inside him. With a final thrust, he came all over his stomach a fourth time and slump on the bed with a tired groan.

“So hot.” Dean rasped out as he turned off the vibrator and pulled it out. He reached his hand out to grip Castiel’s chin and kiss his forehead in a loving manner. “Do you want to get fucked?”

Castiel looked up at Dean with watery eyes and nodded eagerly. His master wasn’t able to hear him with the gag on so Dean removed it. “Yes! Please, master.  I need it.” His jaw felt sore from being open for hours. He didn’t know how much time passed but their scene wasn’t going to end just yet.

“As you wish.” Dean grinned and placed the gag back. He lifted Castiel’s head to make sure the gag was secured and wasn’t too tight around his head. Castiel was shivering in anticipation. The gag became his new favorite toy Dean used on him. It made the scene a lot more fun and exciting. He couldn’t wait to use it again.


	14. Don’t Get too Close

**Summary for the Chapter:**

> Castiel’s curiosities get the better of him.

**Notes for the Chapter:**

> Day 14 of Kinktober- Tentacles

Castiel hummed softly as he picked a blue orchid from the ground and added it to his flower crown. He stuck his tongue out in concentration and held out the finished flower crown with a grin. He was looking for blue orchids all day and finally had enough to finish his flower crown. He walked back to his habitat and took off the flower crown, filled with Jasmines, he was wearing. He placed it next to his other flower crowns and put on the blue orchids. If only he had a mirror to look at himself. He wanted to know how he looked like. He exited his shelter and walked around for a few minutes until he found the lake.

The lake the other nymphs told him about. The forbidden lake. Castiel has heard stories about creatures living among the waters. He didn’t know what kind, and it seems like the other nymphs didn’t know as well. He hesitated and thought it over. He was a curious fellow. He wanted to see for himself if it was true. He took a step forward and walked towards the lake. He looked around with his brows furrowed in confusion.

Nothing happened. Castiel shrugged and looked down at the waters. He smiled when he saw his reflection staring right back at him. He fixed his crooked flower crown and made a couple of faces. He giggled at the funny expressions he was making. Then, he heard water splashing that sounded too close. He looked up quickly and wrapped his arms around himself from fear. He wasn’t a very good fighter. He was still learning, but hopefully, he didn’t need to fight if the creatures the nymphs speak of are actually nice. Castiel always saw the good in everyone.

When he didn’t hear anything else for another ten minutes he looked back at the waters. He reached out and dipped his index finger inside the cool water. He had the sudden urge to get inside and relax. He retracted his hand and undid the knot on his skirt that covered his most private parts. He let the piece of clothing pool around his ankles and stepped into the water. He dipped his head under the water to wet his hair and broke the surface with a gasp. He wiped the water out of his eyes and swam around the lake with ease. He hummed a song that had been stuck in his head for days as he swam around. The water felt cool against his skin, and he didn’t want to ever leave.

He closed his eyes and forgot about his surrounds until he felt something slimy against his arm. His eyes snapped open, and he screeched when he saw a tentacle touching his arm. He tried to swim away but the tentacle tightened its grip around his arm. He started to cry and sobbed when his heart spiked up in fear. He was going to die. Some creature was going to kill him. He should’ve listened to the others. Why didn’t he listen? He was so naive.

“Hey, calm down. I’m not here to hurt you.” Castiel kept his eyes squeezed shut and covered his face with his hands. He ignored the voice that most likely belonged to the creature. He couldn’t stop the tears that streamed down his cheeks and the hiccups that made it difficult to speak. Finally, the tentacle was gone and Castiel felt less scared. He took a couple of minutes to calm down before putting his hands down. His red puffy eyes stared into beautiful green ones that were filled with concern. He took a moment to take in the creature’s appearance. The creature had his hands up and smiled to not scare off the nymph.

“You must be a nymph. That’s so cool!” The creature’s lips pulled back into a full grin. “I’ve never seen one before. I thought you would be...green.” He scrunched up his face in confusion and shrugged. He swam closer to Castiel who shrunk back. The creature stopped in his tracks and held up his hands again. “I’m sorry for startling you. I didn’t know how you would react.” He rubbed his neck and blushed. “Umm...my name is Dean, and you are?”

The nymph stared at the creature with a skeptical look for a few long moments before responding with “Castiel.”

The creature nodded and his smile was back. It was a beautiful smile Castiel had to admit. “Cool! I guess that makes us friends, right?” Dean held out his hand and wiggled his fingers.

Castiel looked down at Dean’s hand and nodded slowly. This creature meant no harm. If he wanted to hurt Castiel he would’ve done it now. “Friends.” He nodded again and grabbed Dean’s hand.

Ever since that day, Castiel always returned to the lake. Throughout the whole month, he learned a lot about Dean. For example, he was an octo. He showed Castiel all of his eight tentacles which made his stomach turn in a good way. The both of them learned about each others’ species and Castiel felt smarter. Despite how close-minded that sounded. The other nymphs have gifts they could use and were far more interesting than Castiel. It was no wonder why he didn’t have a mate. At least now he knew about the creatures in the lake. There were more of them Dean had mentioned. They just never dared to expose themselves. Castiel felt special that the octo decided to show himself.

One day, when Castiel was with Dean at night something clicked. They were playing with each other in the lake. Splashing water at each other; even though it was unfair for Castiel because Dean had ten limbs he can use. One of his tentacles brushed against Castiel’s cock which made the nymph freeze and almost drown. Dean was quick to save him before he could. The octo had worry in his eyes as he squeezed Castiel’s cheeks with his hands.

“What happened?” Dean asked as he looked over Castiel. His touch was very warm compared at the freezing lake. Castiel wanted more.

“I didn’t realize how touch starved I was until your tentacle touched me,” Castiel admitted with a blush. He poked one of Dean’s tentacles just for fun. It twitched and wrapped itself around Castiel’s wrist.

“Oh. Well, I can do something about that.” Dean grinned. He wrapped all eight of his limbs around Castiel’s body and even wrapped his arms around the beautiful nymph. Being engulfed by the creature made Castiel feel so much better. He smiled and laid his head on Dean’s shoulder. One tentacle shifted and brushed against his hardening cock again. He moaned and bucked his hips against the touch. He felt his cheeks heat up and panted quietly.

Dean’s arms tightened around Castiel as his breathing picked up. He cleared his throat, “uh...Cas? Are you okay?” He asked gently with uncertainty. This was Castiel’s chance. All those feelings he developed for Dean needed to come to the  surface.

“I like it when you touch me. I was surprised when your tentacle touched my erect penis. It just felt so good I couldn’t held rubbing against you.” Castiel said softly. He lifted his head and looked up at Dean. He cupped his cheeks and smiled. “Dean. I need this. I’ve wanted this for a while…” he admitted. “But…” he trailed off and chewed on his bottom lip. “You don’t have to do this if you don’t want to.”

Dean felt stunned for two reasons. One, Castiel liked him, and two, did this beautiful nymph just assumed Dean didn’t want this? He responded to that statement with leaning in to kiss Castiel. It was weird and awkward since the nymph didn’t know how to kiss properly, but that was going to change soon. His tentacle wrapped around Castiel’s erect cock and stroked it. The nymph broke the kiss with a loud moan and slump against Dean. He was already so close. This beauty never had an orgasm and Dean was planning to give him many more.

“I’ve wanted this too, Cas.” Dean smiled and kissed Castiel’s forehead. A tentacle made its way towards the nymph’s sensitive hole that might’ve never been touched before. Dean loved that. It just meant that Castiel belonged to the octo now.

“Oh!” Castiel jumped when the tentacle forces its way through his tight hole. He cried out softly and clung onto Dean. His ass ached from being stretched open but loved it anyway. He trusted Dean. The creature wouldn’t do anything to hurt him. Castiel nuzzled into the crook of his neck and huffed as another tentacle made its way into his hole.

Two tentacles pumped into his ass. A liquid was oozing out of the ends to make it easier on Castiel. He was screaming out his pleasure when they kept judging his prostate. Another tentacle stuffed itself inside his mouth. Castiel swallowed up all the liquid it had to offer obediently and sucked on the tentacle with ease. Dean rubbed his sides and cooed softly in his ear. The octo groaned as the two tentacles kept pumping inside Castiel. All of the other tentacles were soothing the nymph and one of them was caressing Castiel’s face lovingly.

“Perfect.” Dean gasped. The praise made Castiel feel all tingly inside. It was the last thing to make him reach his peak. His scream was muffled by the tentacle when he came. The tentacle released his sensitive cock and Dean patted Castiel’s cheek with his hand. He had so much love and affection in his eyes Castiel almost wanted to cry in joy. The two tentacles thrusting inside his hole, one of them inside his mouth, and Dean looking at him like he held the world in his hands. It was all just too much for him. It overwhelmed him. His life was never this interesting.

Dean closed his eyes and moaned. Castiel felt warm fluid inside him and smiled lazily. The tentacles pulled out which made the nymph moan softly. He placed a hand on his belly subconsciously and thought about the children he wants. He will have. Dean’s children. With that thought in mind, he fell asleep with the octo wrapped around him.


	15. More

**Summary for the Chapter:**

> Dean keeps going.

**Notes for the Chapter:**

> Day 15 of Kinktober - Overstimulation

“Please please just fuck me, Dean! I want- I need it so much!” Castiel was practically shaking on the bed with his legs spread out. He stared right into Dean’s green eyes that were filled with lust like his own blue ones. The man had him on edge for about fifteen minutes now. Dean just kept fingering him until Castiel started to beg. “Dean!” He wailed when Dean crooked his fingers to find his prostate. He arched his back and moaned loudly. His stomach was full of his pre-cum. Dean was determined to make him cum a couple of times tonight, and Castiel loved that idea.

“I think you’re ready now,” Dean said with a smirk. Castiel only glared up at him in response. He had been ready a long time ago. Dean just liked to draw it out when he had Castiel like this. A begging and moaning mess. His hair stuck to his forehead and a bead of sweat streamed down his face. He ignored it as he leaned on his elbows to push back against Dean’s fingers. He whined when the man took out his fingers. His hole clenched around nothing and he thrashed against the bed.

“Calm down, baby.” Dean cooed softly as he grabbed the bottle of lubricant. He drizzled the lube onto his hand again to coat his cock. He scooted closer to Castiel and pushed his legs up to his chest. He practically bent Castiel in half when he draped his body against his boyfriend’s. He rubbed the head of his cock against Castiel’s hole and pushed into him with ease. He groaned and prepped Castiel with kisses all over his face to calm him down.

Tears of pleasure were squeezed out of his eyes at how felt it good when Dean was inside him. He gripped the back of his knees and kept his legs spread as Dean wasted no time and pounded into him. The headboard smacked against the wall with the force of Dean’s thrusts. Castiel threw his head back against the pillow and screamed out his pleasure. He wailed when his orgasm was ripped out of him. He came untouched all over his stomach and he clenched around Dean’s cock. He’s used to being a bit sore because Dean lasts a while.

“We’re not done yet, sweetheart.” Dean murmured as he shifted his position to strike Castiel’s prostate. He screamed and arched against Dean.

“It’s too much. Too much, Dean.” Castiel sobbed and threw his head from side to side. His legs started to shake from the overstimulation Dean was giving him. It felt so good and intense. He didn’t know if he wanted to squirm away or come closer.

“Almost there.” Dean groaned as he thrust into Castiel a couple of times and came. Castiel sighed softly and dropped his legs. He whined when Dean pulled out and closed his eyes lazily.

He stayed still for a couple of minutes until he felt Dean manhandled him onto his stomach. Dean gripped the globes of Castiel’s ass and examined the cum leaking out of his hole. “Dean- Dean what are you doing?”

“Shhh, baby.” Dean wanted to keep going. He has Castiel all spread out in front of him and dives in between his cheeks to lick him out. He prodded Castiel’s hole with his tongue until it passed through the ring of muscle.

Castiel reached behind him and gripped a handful of Dean’s hair. “No more. No more. Dean! It’s too much.” He sobbed as his body shook with so much pleasure.

Dean pulled away and rubbed Castiel’s soaked hole with the pad of his fingers. “Just one more, baby. You can do that, can’t you?” Dean cooed. When Castiel nodded and whined in response Dean dove in again. Castiel jumped and pushed back against Dean’s face. He could barely breathe. He breathed in so little air as broken moans passed his lips.

“M-More.” Castiel sobbed out. He gripped the thin sheets and curled his toes as Dean kept assaulting his sore hole. He was going to get bruises on his ass for how tight Dean was gripping him and just enjoying the taste of his boyfriend. He added two fingers along with his tongue and thrust them into Castiel until the man came with a muffled shout against the mattress.

Dean laid down next to Castiel and wrapped his arms around him. Castiel turned in his grasp and winced. He looked up at Dean with dazed eyes and a shy smile. He laid his head on Dean’s chest and felt sleep weighing down on him until he fell asleep from how tired he is.


	16. Grind Against Me

**Summary for the Chapter:**

> Castiel wants Dean’s attention.

**Notes for the Chapter:**

> Day 16 of Kinktober - Frottage

Castiel propped his cheek on the palm of his right hand as he stared at the clock on the wall. He tapped his foot and waited for the big hand to land on the twelve. He wanted to leave work the second he stepped into the coffee shop. It didn’t help that the regular customer who has the biggest crush on him tried to get his phone number. He tried his best to ignore the customer but felt like a bad employee. He needed this job to pay for his classes since his parents didn’t bother to; ever since they found out about his sexuality.

He sighed heavily and put his head down. He didn’t hear the bell ring for the last couple of minutes thankfully. When his phone buzzed he shot up and turned off his alarm before dashing out the door. He turned off the lights and locked the shop before heading his way towards his car. He slid inside the driver’s seat and turned on the engine. He backed out of the driveway then headed towards his boyfriend’s apartment where he’s staying at for now. Once he made it at his destination he parked his car in the usual spot. He turned off the car and stepped out of it. He climbed up the stairs two at a time and reached into his pocket for the keys. He unlocked the door and pushed it open.

“Dean, I’m home!” Castiel called out to his boyfriend as he shut the door behind him.

“I’m in the bedroom!” Dean called back. Castiel smiled and left his trench coat in the living room before heading his way into the bedroom. He found his boyfriend sitting by the desk doing boring paperwork. He looked at Dean’s body and bit his lip. He missed him so much and was in a mood for some fun, but Dean didn’t even pay attention to him. He was too engrossed in the papers in front of him.

“What are you doing?” He asked as he leaned against the doorway.

“I’m doing paperwork for the garage.” Dean lifted a paper with the garage’s symbol on it and tiny words Castiel could barely see from his perspective.

Castiel walked closer and pulled Dean’s chair to make room to sit on his leg. He poked his boyfriend’s cheek continuous until Dean turned his head with a raised eyebrow. “What are you doing, sweetheart?”

“I want you to pay attention to me. Take a break. I’ve had a boring day at work today.” Castiel pouted and flicked Dean’s ear playfully.

“That sounds nice, but I’m busy, honey. Let me just finish this, okay?” Dean reached around Castiel to finish filling in the paperwork. He didn’t mind his boyfriend sitting on his lap. It felt nice to be able to touch him after being apart for so long.

Castiel pouted and started to grind against his thigh. He let out a quiet moan and dropped his head on Dean’s shoulder. “Please touch me, Dean.” He said as he looked back up at his boyfriend through his thick eyelashes  and tried to be seductive.

Dean’s chuckle was the response he got since Dean knew how embarrassed Castiel is now. “You started this baby. Finish it.” He whispered and licked his lips. He leaned back in his seat to just watch his boyfriend squirm on his lap. He winked and leaned in to place a rewarding kiss on Castiel’s lips. He tried to chase Dean’s lips when the man pulled away but was stopped with a hand on his chest. “What did I just say?” He asked with a raised brow. Castiel pouted and placed his hands on Dean’s chests. He had to admit that being watched by Dean felt hot.

He started to grind against Dean’s thigh again. It felt so good despite the number of layers they had on. He let out a high pitched whine and squeezed his eyes shut. His boxers were getting soaked from the pre-cum while grinding his clothed cock against Dean’s thigh. Dean’s intense gaze was also a plus. Castiel’s face started to glow red and he started to sweat. He wanted to take his clothes off but didn’t want to stop his grinding.

“That’s right, baby. I can see you’re already close. Come on, Cas. Cum for me.” Dean whispered in Castiel’s ear. He ignored his own arousal while he talked to Castiel towards the edge. The man tensed up and came inside his jeans with a loud moan. He panted and slump into Dean’s grasp. Dean ran his fingers through Castiel’s hair and whispered praises into his ear. “You did so well, baby. I’m proud of you.” He smirked mischievously. Maybe he should be busy more often if Castiel acted like this without receiving attention. He truly loved this side of Castiel.


	17. My Omega

**Summary for the Chapter:**

> Dean would do anything to get the omega of his dreams.

**Notes for the Chapter:**

> Day 17 of Kinktober - Collaring

Dean had spotted Castiel in tears at the crack of dawn. Apparently, he was staying over the night but had gotten into a fight with Sam. He didn’t hear much but it was obvious enough Sam hurt Castiel a lot and refused to talk it out. Typical of him. He didn’t deserve the omega who was head over heels for Sam; the wrong brother.

The alpha shuffled into the room quietly and sat down next to Castiel. The younger man sniffled and tried to wipe away the tears. Dean tried to make him feel better by wrapping him in his scent. He scooted closer to him and the omega looked hesitant. Dean couldn’t blame him. Sam gets possessive. Not because he didn’t want others to flirt with Castiel only because of his alpha pride. He knew his brother better than anyone.

“Are you okay?” Dean asked gently as he placed his hand on top of Castiel’s. He offered the omega a polite smile, just trying to be friendly. Castiel relaxed into his touch when Dean confirmed it was a friendly gesture, for now.

“Yes. This isn’t the first time.” Castiel sniffled as he rubbed his eyes with his unoccupied hand. Dean still hasn’t removed his hand as they talked. The more they talked the more Dean grew to like Castiel a little too much. He was so cute and adorable when he isn’t crying. The alpha just wanted to kiss those pouty lips, but their moment was ruined when Sam came into the room. Castiel moved his hand away and stood up from the sofa.

“I’m sorry, Castiel. I don’t know what came over me. Forgive me?” Sam spread his arms and smiled when Castiel immediately ran into his arms. The action made Dean’s insides burn with jealousy. At that moment, Dean knew his obsession with Castiel would only grow if he didn’t get his hands on him.

It always started this way every time Sam and Castiel fought. Well, it’s mostly Sam bringing up problems and yelling at Castiel who stays quiet. Dean is always there to pick up the pieces and confronts the omega when needed. The thing they developed was love, Dean knew it, but Castiel was in denial. He believed that all the love he has is for Sam, but is it really? Dean could see it. Sam was the toxic one who made up the drama with every little thing. It started to annoy Dean but mostly upset him. He hated seeing Castiel cry; thinking it was his fault for the fights. All the alpha wanted to do was steal Castiel and give him the world because he deserved it. Sam didn’t deserve him. With that thought in mind, Dean’s anger and hatred for his brother grew. They never got along with each other in the past and didn’t even try now. The only reason why Dean visits Sam was because of Castiel. Only him. He didn’t even bother to strike up a conversation with his own brother.

Dean gripped the handle of his knife and glared at the closed door in front of him. The adrenaline in him made him continue with his egregious plan. He reached out and turned the doorknob to push open the door. He walked towards the edge of the bed and towered over the sleeping form of his brother. He lifted the blade and, in one swift movement, he struck Sam on the chest, killing him instantly. His hands were covered in blood when he pulled out the blade. He grinned nastily as he left the body behind and headed towards the kitchen. He turned on the sink water and cleaned the blade. He turned off the water and placed the knife back before grabbing a rag to clean the blood off his hands.

Dean grabbed a glass and filled it with water. He reached into his pocket for the pill that was covered in paper. He had done some research on this drug and hoped it was worth his money. He dropped it into the water and took the glass to the guest bedroom where Castiel was staying at. He entered the room and sat down next to Castiel’s body. He watched over the man sleep and smiled at how peaceful he looked. He truly was beautiful. Dean reached out and gently stroked Castiel’s cheek.

The omega sighed softly and fluttered his eyes open. “Dean?” He whispered and yawned.

“Hey, sweetheart,” Dean whispered as he handed Castiel the glass of water. The omega looked at him in confusion before sitting up to grab the water. He smiled in thanks before downing the glass in one go. He wiped his mouth as he handed the glass back to the alpha. Dean placed the glass down and wrapped his arms around Castiel. The omega whimpered as his vision started to blur. He felt all tingly inside when the alpha wrapped his arms around him. So many thoughts were going through his head about this, but one thought stood out.

“Dean…” Castiel whined and looked up at the alpha with big eyes. “Dean. Please fuck me. I need it so much. I-I’ve wanted you for so long.” He nuzzled into the crook of Dean’s neck and inhaled his scent.

The drug was activating just as Dean’s research said. It brought a smile on his face. He took off his shoes and climbed under the covers with Castiel. He petted the omega and kissed his forehead. “Not tonight, baby.” He hugged Castiel close to him and sang him a lullaby until the omega fell asleep. He wouldn’t do anything with him today. It just isn’t right to have sex with a drugged omega no matter how prettily he begged.

Dean left Sam’s body behind and moved to the other side of the country with Castiel. They changed their identities and were happy together. The omega was still kept in the dark about Sam’s fate. Dean didn’t quite know how he would react. It didn’t matter though. The past needed to stay in the past.

Dean was sitting on a chair; filling up an application for a job that caught his eye. While he wrote down his information he reached out with his other hand and patted Castiel’s hair. The omega purred and leaned into the touch. He was kneeling beside Dean naked except for the collar he was wearing. He was also very pregnant with Dean’s pups. Despite the situation, Castiel’s was truly happy and would follow his alpha anywhere.


	18. New Ideas

**Summary for the Chapter:**

> Castiel suggests they switch roles.

**Notes for the Chapter:**

> Day 18 of Kinktober - Role Reversal

“I feel like we should switch our roles.” Castiel thought out loud mindlessly as he grabbed the wooden spoon and stirred the soup he was making.

Dean lowered his cup of coffee and quirked an eyebrow. “What do you mean by that?” He turned his body towards Castiel.

“Maybe this time I can be the dominant one,” Castiel suggested with a shrug. He could see the hesitation on Dean’s expression and he smiled to calm the man’s nerves. “You’ll still be the one inside me, of course. I love being stuffed by you.” He winked and giggled. “I just meant. I can tie you up and ride you all day. Just a suggestion.” He mumbled the last part inaudibly as he looked down at the soup.

That idea doesn’t seem so bad in Dean’s mind. He always loved to take control, but if Castiel wanted to try it out then why should he deny it? They are exploring new things. “Sure. You have to promise to be careful though.” He smiled encouragingly and stood up from the chair. He walked towards Castiel and wrapped his arms around him. He propped his chin on Castiel’s shoulder and watched him stir the soup.

“I will! Don’t worry. I’ll take care of you like you take care of me.” Castiel reached out and patted Dean’s cheek before turning his head to kiss his lips. He sighed as he turned off the heater. “Now, are you ready to eat before we try it out?”

“Definitely, baby.” Dean wiggled his eyebrows and pulled away from Castiel to grab the bowls. Castiel giggled and watched him move around the kitchen so easily.

-

Castiel was full of excitement when he saw Dean laid down on the bed. They were both currently naked and about to try out this role reversal he had suggested. He was frozen in place for a couple of minutes. This was his first time actually being the dominant one. He had taken a long time to finger himself open because the butterflies in his stomach wouldn’t stop. All his worries went away when Dean looked up at him and smiled; his face was full of trust. He trusted Castiel. This encouraged him to reach out and grab the rope that was beside Dean. He smiled back at the man and stepped forward to tie his wrists to the headboard. Dean let himself get tied up and felt his muscles relax instantly. The both of them were enjoying this so far.

Castiel looked at the black box on the nightstand and chewed on his bottom lip. He already knew what he wanted to put on Dean. He took off the lid of the box and reached inside for the cock ring. He had worn this so many times he loved it. He always came hard when Dean put this on him, and now he wanted the same treatment for the man. He put the lid back on before grasping the cock ring and securing it on Dean’s hard cock. He was having the same effect on seeing Dean like this. All laid out in front of him. Dean clenched his hands and looked up at the ceiling. He felt Castiel get on the bed and straddle his waist. He looked at him and smiled. The cock ring felt odd on him since he never wore it, but he knew he’ll grow used to it and love it.

Castiel grasped Dean’s cock and raised to his knees to line his cock up. He slid down on Dean’s cock with a quiet moan. He placed his hands on Dean’s chest and gasped. His thighs quivered when he rose up to his knees to slam back down. Dean threw his head back against the pillow and groaned. He wanted to put his hands on Castiel but the rope stopped him from doing that. He whimpered and his breathing started to pick up. His cock was sensitive and all he could do was thrust up to meet Castiel’s movements.

“Yes! I love it when you squirm.” Castiel chuckled when he looked down at Dean struggling with the restraints. He didn’t stop his movements one bit. His thighs started to burn but that still didn’t stop him. Dean planted his feet on the bed and thrust upwards making Castiel screamed for hitting his prostate. “Right there!” He looked up towards the ceiling and moaned loudly.

He had cum at least three times. No matter how sensitive he got he kept riding Dean’s cock. It just felt so good to him and it looked like Dean was enjoying it as well. “We should’ve done this a long time ago,” Castiel said. His arms started to shake from their position on Dean’s chest as his movements slowed down. The best part of this was that Dean was way more vocal. He babbled nonsense when Castiel squeezed around his cock just right.

Castiel got off Dean and took off the cock ring. He only needed to stroke him once before Dean started to cum. Long strips of cum landed on his stomach, chest, and even his chin. The man panted heavily and slumped on the bed. Castiel wiped away the tears and untied him from the headboard. He leaned forward and placed kisses all over Dean’s face. “That was amazing, Dean.” He whispered and grinned when he got a shy smile in response. Now it was his duty to help shower Dean and feed him something. Castiel found himself loving every second of it.


	19. Daddy’s Cock Warmer

**Summary for the Chapter:**

> Dean wakes up his boy with sex.

**Notes for the Chapter:**

> Day 20 of Kinktober - Cock-warming

Dean woke up slowly. He groaned softly as his eyes fluttered open. The sun was still hidden behind the clouds based on how dark it was. It took him a full minute on why he woke up so early; he’s hard. His cock is buried inside Castiel who’s still sound asleep. He always treated him like a cock warmer whenever he felt like it. Castiel loved it so much. He was the perfect cock warmer for his daddy. Whenever Dean was doing some work he would have Castiel underneath his desk with his cock inside the boy’s mouth. He stayed there on his knees until Dean felt like fucking into his mouth and down his throat. Sometimes he had the boy sitting on his lap with his cock inside him. Castiel would just snuggle into him and nap while Dean did his work. It was their favorite thing to do; with Castiel having a vacation from school and Dean being busy with work.

He wrapped his arms around his baby boy and circled his hips. He muffled a groan when Castiel immediately clenched around him. The boy sighed softly and burrowed into the sheets in his sleep. He looked so cute when he’s asleep. Dean placed a hand on his hip and roamed his body. He touched every patch of skin he can reach and thrust forwards. The boy whimpered and shifted slightly. He thrust back against Dean subconsciously and his lips parted with a gasp. Dean brought a hand up towards his chest and started to rub over a sensitive nipple. He kept thrusting into his boy until Castiel finally woke up.

“D-Daddy?” He gasped as he gripped Dean’s hand and thrust back against him. He whimpered tiredly and lifted his leg.

“Morning, baby,” Dean whispered. He gripped Castiel’s thigh and lifted his leg higher to thrust at the right angle. His boy let out a scream and moans were followed after that.

“Feels so good to wake up like this daddy,” Castiel said with a tired smile. His black thick hair was sticking up in all directions and some of his hair was plastered against his forehead.

“That’s a good boy.” Dean murmured against the back of Castiel’s neck. He breathed heavily against his boy’s neck as he kept going. He lowered his hand to wrap it around Castiel’s cock and tugged on it. The boy arched his back and shook in Dean’s grasp.

“Yes, daddy!” Castiel gasped and dug his fingernails into the skin of Dean’s hand. He didn’t mean to, but it was just getting too much for him now. He tried to hold off his orgasm until his daddy told him he can cum. “Can I cum, daddy? Please! I’ve been a good boy. I’ve been a good cock warmer for you.”

Dean smirked and kissed Castiel’s cheek. “That is right, baby. That’s why I’ll let you cum. Cum for me, baby boy.” He picked up his pace and stroked Castiel faster until the boy tensed up in his grasp and came all over his hand. “That’s a good boy.” Dean patted Castiel’s hair and groaned when his boy clenched around his cock. He came inside Castiel. The boy sighed softly at being filled and relaxed into the mattress.

Dean didn’t pull his soft cock out. He stayed, attached to Castiel and closed his eyes. “Go back to sleep, sweetheart. We’ll do round two when you wake up again.”


	20. Phone Sex

**Summary for the Chapter:**

> Castiel texts Dean to distract himself.

**Notes for the Chapter:**

> Day 20 of Kinktober - Dirty Talk

Castiel threw his homework in frustration and sighed heavily. He leaned back against his bed and stared up at the ceiling. He blew out a puff of air and drummed his fingers against his belly. He suddenly regretted taking AP classes. They were so stressful and always gave packets upon packets of homework. Nobody learned that way, in Castiel’s opinion. He needed to take a break. A distraction from all the stress that was trying to consume him.

He turned his head to the side and stared at his personal device with an interesting thought in mind. He chewed on his bottom lip as he thought about his choice. So many thoughts were going through his mind. “Oh, fuck it. I’ll just do it,” he sighed as he reached out for his cell phone. He grabbed it and turned it on. The screen lit up, and he immediately went to the message app to text his boyfriend.

_ “What are you doing?” _

He exited the app and opened his Instagram app to scroll through his feed while he waited for Dean to respond. A couple of minutes later he received a message from him and smiled. He tapped on the notification and read the text.

**“I’m watching TV with my little brother. It’s boring. I don’t even know what’s going on.”**

_ “Aw, poor baby.” _

**“Shuddup. What are you up to?”**

Castiel snorted at the text he received from Dean and grinned.

_ “I was doing homework, but I need a distraction.” _

Castiel chewed on his bottom lip again as he slowly typed up another message before Dean could see the one he just sent. He took a deep breath and sent it when he was done.

_ “I have a suggestion on what we can do? ;)” _

**“Oh? What is it, sweetheart?”**

Dean’s nicknames for him made Castiel swoon. His heartbeat spiked up, and he felt like he was about to throw up the butterflies in his stomach.

_ “I want to call you. I want to hear your voice. It turns me on.” _

The three dots showed up a couple of times and Castiel was losing his confidence until Dean sent his message.

**“Fucking hell, Cas. Sammy was right next to me. I had to make an excuse to go to my room.”**

Castiel giggled. He felt another boost of confidence as he typed out his message.

_ “Good. That means you can talk dirty to me on the phone.” _

Immediately after Dean read the message Castiel’s phone buzzed in his hand. He jumped and answered the call quickly. “Hello?”

“Are you  _ trying  _ to get yourself in trouble?” Dean’s gruff voice sounded through the other end which made Castiel’s whole body shiver. He could feel himself hardened in his shorts just by hearing his boyfriend’s deep voice.

“Maybe? I’m just really horny and bored.” Castiel sighed as he laid down on the bed he spread his legs out in front of him and rubbed his cock through his shorts. A not so quiet gasp slipped through lips at the contact.

“Are you already touching yourself, Cas?” Dean’s breath hitched.

“Yesss.” Castiel closed his eyes and unzipped his shorts. He slid them down and kicked them off along with his underwear. His cock sprung against his stomach in interest.

“Okay. I want you to keep touching yourself. Imagine it’s my hand while I kiss you to try and distract you. Distract you from my fingers stretching you out for my cock.”

Castiel wrapped a hand around his cock and started to stroke himself while Dean kept talking dirty into his ear. He let out pathetic whimpers and wished that his boyfriend was here. “Ah! Dean. I miss you,” he whined.

“I miss you too, baby.” Dean rasped out. Castiel could hear his breathing picked up just slightly. The thought of Dean masturbating with me sent a shock throughout his body. “Once you’re nice and stretched out I would ram into you and fuck you so hard you won’t be able to walk properly the next day.”

That sounded a very good idea in Castiel’s mind. He always loved how hard his boyfriend would fuck him and leave bruises all over his body.

“I would suck on your neck and mark you up to let everyone know you’re mine,” Dean growled softly. Castiel keened and arched his back as he came all over his soft tummy. He heard Dean groan and smiled lazily. He brought his hand up to his lips and licked his hand clean. He also sucked on his fingers.

“Are you tasting your own cum? Fucking hell, Castiel.” Dean groaned. Castiel giggled.

“Thank you for this, Dean. Now I have to go do my homework.”

“You’re welcome, baby. Finish your homework, and I’ll reward you tomorrow when I see you.”

“Goodbye, Dean.”

“Bye.” Castiel hung up his phone and laid on the bed for a couple of minutes before continuing with his homework.


	21. The Brand of an Angel

**Summary for the Chapter:**

> Castiel gets Dean’s handprint on his arm.

**Notes for the Chapter:**

> Day 21 of Kinktober - Branding

_ Castiel was practically shaking from head to toe, and not just from the cold. He was barely wearing any clothing when he scooted towards the corner of the room. He wrapped his arms around himself and shielded his body away from the other angels in the room. He was shaking from the cold and the fear that was consuming him. All the other angels were huddled together while he was alone. He was a nobody just like the other foot soldiers in the cell. It’s no wonder why the archangel wanted them. He finally thought he was recognized. So much for how naive and innocent he is. _

_ The cell gate opened and Castiel jumped. He propped his chin on his knees and lowered his eyes towards the ground. The archangel’s presence was much closer and stronger when his shoes came into Castiel’s point of view. He hesitantly looked up into those green eyes and gulped. The archangel motioned him to get up and turned around. Castiel scrambled to get up and followed him quickly. He didn’t want to be stuck in this cell anymore. Dean led him into another room and gestured towards the table full of blood. Castiel’s eyes darted to the pile of bodies with burnt out eyes and gulped thickly. He laid down on the table and willed himself not to cry from fear. _

Castiel opened his eyes and sighed quietly. He knew he was crazy for thinking about their first encounter. At that moment, he was scared for his life and wanted to be as far away from Dean as possible. Now, all he wanted to do was be on Dean’s side. No matter where the archangel decided to sit him at. He mostly made him sit on the ground next to his feet or on his lap when he’s feeling excited. Their first meeting made Castiel feel alive. He finally had a purpose in life. Everybody knew him, and the most important thing was that he loved serving Dean. It was like a dream come true for him.

He was currently chained to the brick wall. A chain was attached to his collar Dean made specifically for him. He was waiting for the archangel and thought about what he was going to do when he got back. Whatever it was, Castiel would take it like a good boy he is. He just hoped he wasn’t angry. The last time they had sex with Dean being angry he had hurt Castiel. From then on, they promised to not have sex while either one of them is angry. He had been thinking about it all day. His cock was hard, and he so badly wanted to touch it, but Dean’s rules wouldn’t let him.

About an hour later Dean finally came back. He took off his hat and smiled when he saw the little angel. His gaze immediately went to Castiel’s hard cock which made the angel flustered. “I have another thing in mind, sweetheart.” Dean said as he took off his suit jacket. He rolled up the sleeves of his white dress shirt and walked towards Castiel. He freed him from his restraints and led him out of the cell. He sat down on the bed and let Castiel slid into his lap.

“And what’s that, sir?” Castiel asked with big wide eyes. Dean smiled and cupped his cheek. He looked so cute.

“I’m going to brand you.” Dean’s response was almost a whisper, but Castiel heard it all right.

His eyes widened a bit at the suggestion. He tilted his head to the side and squinted his eyes. He has heard of angels branding other supernatural creatures or humans. He didn’t think Dean was into that. He never asked, and he didn’t want to anger the archangel. It was almost a surprise for him since Dean was the one who brought it up. The thought of being branded and  _ owned  _ sent a shiver through Castiel’s body.

He smiled weakly and nodded. “I’ll like that,” he whispered gently and wiggled on Dean’s lap. Being owned by the king of Heaven was a good thought in mind.

“Good.” Dean smiled. “I’ll need you to relax, okay?”

Castiel nodded, “okay.”

  
He placed a hand on Castiel’s shoulder and shut his eyes tightly. He was focusing on his grace and felt it hum inside him. He felt it flow through his veins as he concentrated on the mark. Pain showed on his facial features but it went away just as quickly as it came. He didn’t need to feel weak just to mark an angel. An angel that wasn’t even as strong as him, but it was proven to be difficult with the amount of grace he needed to use. He knew this must be hurting Castiel as well, but he wasn’t very concerned. The angel loved the pain that came with everything Dean has done on him. He was able to sense a bright light coming from his hand, but he didn’t dare open them. So many things could go wrong if he didn’t fulfill the branding. He didn’t  _ know  _ could go wrong since every angel was careful, and he did not want to know what would happen. He wasn’t stupid enough for that.   
  
A few long minutes later, it was over. Dean felt a bit drained but otherwise felt well. He didn’t care about that. He would recharge later on, and nobody was stupid enough to challenge him anyway. He finally opened his eyes and stared at his hand on Castiel’s shoulder. He cradled the weeping angel’s head and pulled him towards his chest. He petted his hair as he removed his other hand. On Castiel’s shoulder was an imprint of Dean’s hand. It was proof that this angel belonged to the archangel no matter what, and nobody could break their profound bond. Now, they just needed time to strengthen it.

“Thank you! Thank you!” Castiel cried as he nuzzled into the crook of Dean’s neck. He sobbed and shook.

Dean wrapped his arms around the angel and sighed tiredly. He felt a wet spot on his dress shirt and smirked. “Did you cum from the brand?”

Castiel’s body stopped and he pulled away from Dean. He lowered his eyes in submission and nodded slowly. “I’m sorry, s-sir.”

“It’s okay. I’ll let this one slide. Rest, my angel.” Dean laid Castiel down on the bed and kissed his forehead.


	22. Bruises and Kisses

**Summary for the Chapter:**

> Gabriel thinks Dean is abusing Castiel when he sees the bruises.

**Notes for the Chapter:**

> Day 22 of Kinktober - Impact play

Gabriel heard someone walked in and looked up from the TV. He looked over at the front door where Castiel was letting himself in with the key to their apartment. Castiel smiled at his brother then frowned when Gabriel was glaring at his neck. He brought a hand up to the neck and massaged it. His eyes fluttered shut when he felt a sting of pain. He was slightly pressing down on the bruises and hickies Dean left him. He loved it. He opened his eyes and pulled his hand away when he found Gabriel still staring.

“Hello, Gabriel.” He smiled and walked towards his bedroom. Gabriel stared after him as many scenarios went through his head. One particular thought stood out; he came to the conclusion that Dean was abusing his baby brother. The nerve of him. He reached into his pocket for his phone and dialed his friend’s number. He held the device to his ear and waited for him to pick up.

“Hey. I need a favor.”

-

Castiel knocked on Dean’s door and stood on his tippy toes as the man opened the door. He smiled and wrapped his arms around his neck to bring him down for a kiss.

“Hello, to you too.” Dean chuckled as he carried Castiel into his house. He kicked the door shut and continued with their make-out session. He forced his tongue inside the man’s mouth which made him whimper. “Mmm. I love your noises,” he winked.

Castiel giggled and played with Dean’s hair. “If you want to keep hearing me making those noises then we should move to the room.” He wiggled his eyebrows suggestively. Dean moaned quietly just by thinking about what they’re about to do. He picked Castiel up and carried him into the bedroom. He practically threw him on the bed before climbing on top of him.

“Tell me how badly you want this.” Dean rubbed a thumb over Castiel’s bottom lip. When he didn’t respond Dean brought a hand down and slapped Castiel across his face. He gripped a handful of his shirt and brought him close to his face. “Tell me.”

Castiel let out a sharp cry and felt his cock jump in interest. His cheek burned with the slap, and he loved it. “I want it so bad! I love it when you treat me badly, Dean.” He felt flushed from what he said but squashed down the shyness and hesitation. He closed his eyes and panted heavily. He felt Dean wrap a hand around his throat and keened at the contact. The man was only rubbing a thumb over his pulse. He huffed in frustration, but before he could comprehend what was happening Dean’s weigh was off of him. He opened his eyes and saw Dean and Gabriel stumbling onto the floor and throwing punches at each other.

Castiel scrambled off of the bed and stood up on wobbly legs. “Gabriel! What are you doing?!” He grabbed his brother’s arm and tugged him off. Once they broke apart he helped Dean up and cupped his face to examine any bruises or cuts. He was clean except for a few scratches that would go away later. Meanwhile, Gabriel was sporting a black eye and held his dislocated shoulder. Castiel felt guilty for caring about Dean more even though he knew his boyfriend was a great fighter. It was so unexpected though.

He turned towards Gabriel and glared at him. “What is the meaning of this? You better have a good explanation!” He crossed his arms over his chest.

Gabriel looked between the pair with confusion written on his face. Dean and Castiel were both glaring at him. “Of course I do! Dean just hit you!”

Castiel tilted his head to the side and felt his cheeks heat up. He cleared his throat awkwardly and fiddled with his fingers. How was he going to explain this? “Well…” he drawled out awkwardly. He glanced over at Dean momentarily then looked back at Gabriel and sighed. “We’re doing a sex scene.” He blurted out.

Gabriel raised an eyebrow. “Why would you want to do something like this? Did Dean suggested it?”

“No, I did.” Castiel’s face started to heat up. “Dean was skeptical at first because he doesn’t like the thought of hurting me, but I wanted to do it so badly.”

“How can you think so low of me?” Dean asked after a while of being silent. He was glaring daggers at Gabriel who finally understood his mistake. He misunderstood.

“Ooohhh. Sorry?” Gabriel grinned awkwardly. Dean pushed him out of the bedroom and towards the front door. Castiel quickly followed behind. “Hey! Can you at least fix my shoulder?”

When Gabriel was outside Dean put Gabriel’s shoulder back in place who groaned in pain. He slammed the door on him and turned back to face Castiel. “I’m never forgiving him for that.”

“I’m sorry, Dean.” Castiel sighed as he placed his hands on Dean’s chest. “I don’t know what he was thinking.”

“It’s okay. I guess I kinda get it. He’s protective of you.” Dean smiled and stroked the cheek he slapped Castiel on.

“Let’s stop talking about him and continue with our scene, yeah?” Castiel grinned and turned around to walk back to the bedroom. He swayed his hips back and forth and Dean scrambled to follow after him. They stumbled onto the bed with Castiel giggling as he threw his arms around Dean’s neck.

“What do you want to use today?” Dean asked as he kissed Castiel’s neck.

“The cane,” Castiel said confidently as he leaned his head back against the pillow.

Dean pulled away and got off the bed. “Alright. I want you naked once I find it.” He walked over to their closet and dug around to find the cane. They had many toys in the closet. They made sure to hide them if people wanted to snoop. He grabbed it and turned around. He smiled in approval when he saw Castiel naked and sticking his ass out in the air. The side of his face was laying on the bed as he waited for Dean. “Good boy.” He hummed. He walked closer and laid the cane on Castiel’s ass.

The touch made Castiel shiver. The sting of Dean slapping him was gone, and he wanted more. Dean tapped the cane against Castiel’s ass a couple of times before hitting him hard. The man arched his back and moaned. Dean rained down the smacks on Castiel’s ass and even his back. He was sweating and he felt pain and pleasure all over. Tears of pleasure streamed down his cheeks and onto the bed. “Ahh! Dean!” Castiel sobbed and bit down on the sheets. He breathed heavily through his nose and heard the smacks echoed.

When Dean reaches twenty hits he stopped and dropped the cane on the floor. Castiel’s ass was full of bruises and there were some minor ones on his back. He kneeled on the bed and started to kiss every bruise Castiel had. The man started to cry silently and winced every now and then when Dean kissed just a little too hard. He laid down next to Castiel and held him close to his chest.

“You did so good baby.” Dean praised him and smiled as he kissed his forehead. Castiel smiled sweetly at him and nuzzled into his chest.


	23. Red Riding Hood

**Summary for the Chapter:**

> Castiel wanders off to follow a bee.

**Notes for the Chapter:**

> Day 23 of Kinktober- Size Difference

The boy hummed a tune quietly to himself as he skipped and swung his basket back and forth. He did a little twirl and spread his arms out. He grinned when he saw a bee fly past him. He giggled and started following it. His mission to go to the village slipped out of his mind as he followed the bee. It buzzed past his ear and landed on a flower. He crouched to examine the beautiful flower. He wanted to pluck it to give it to his grandmother. When the bee flew away he reached out and tried to rip it from the ground. It was proven to be difficult. He knew he wasn’t that strong, but it shouldn’t be difficult for him to pluck a single flower from the ground. It was alone. No one was taking care of it except for the sunlight and rain. He planted his feet on the ground and tried to lift himself up with his legs. He let go of the flower and fell onto the ground with a huff.

He was about reach out and try again when he heard a twig snap. He scrambled to get up on the floor and looked around. His legs started to shake as the fear ate him up. When he didn’t see anything or anyone he looked down at the beautiful flower. He wondered why it was so hard to get out. He grabbed his basket and frowned. He was sad to leave it. He turned around and was able to leave when he heard something rustle behind him. He turned around quickly and bit back the scream. He placed a hand on his chest and huffed out a breath of air.

“You scared me half to death!” Castiel glared at the big wolf that walked closer to him. The wolf grinned and licked up Castiel’s face. “Bleh!” The boy said when he wiped off the saliva. He reached out and scratched behind the wolf’s ear. He giggled and smiled at the animal.

The wolf took a couple of steps back and transformed back into his human form. Castiel blushed when he saw Dean naked right in front of him. The man was always naked. He had no shame, but Castiel was never used to it. “What did you bring me something?” Dean asked hopefully as his eyes darted to Castiel’s basket in mind.

“Of course,” he nodded. He grabbed a muffin and handed it over to Dean who ate the bread quickly. The man licked his lips and moaned. He looked down at the boy who blushed even more.

Dean winked. “I think you brought me something else.” He walked closer to Castiel.

“I do?” He asked with an innocent face and tilted his head in question.

Dean laughed and stroked Castiel’s rosy cheek. “I’m pretty sure.” He licked over his canines and engulfed the boy into a hug. He leaned in and kissed him deeply. Castiel melted into his grasp and grasped his biceps. They were so strong from under his touch. He loved it. Dean pulled back to lay Castiel on the grass. They were used to making love outside in the wilderness. The boy’s grandmother would throw a fit if she ever found out about their relationship. Dean made quick work on the red cloak and the dress Castiel was wearing. He left the cloak under the boy and rubbed a dry finger against Castiel’s rim. The boy arched his back and moaned. Both of their cocks were already hard from the kissing.

Dean pulled his hand away and glanced towards the basket. He looked into it for the lube and smirked at the blushing boy. “Cherry flavored. I like.” He chuckled huskily. He poured some lube onto his hand and rubbed his fingers together. He reached in between Castiel’s thighs and towards his hole again to push in a finger. He prepped the boy slowly and gentle like always. No matter how big and scary looking Dean looked he always took care of Castiel. The boy moaned quietly and closed his eyes. He was shaking in anticipation. He had waited a long while for this. His grandmother didn’t let him out in the winter. He was so glad the season was over. He was able to spend time with Dean again.

Once the man was done he coated his cock before pushing into Castiel. The boy tensed up then relaxed immediately when Dean started to rub his belly. He sighed quietly as Dean pushed his big cock inside him. He loved how big the wolf was. After every time they had sex Castiel couldn’t walk properly for a couple of days. Dean’s cock filled his small body so good. He wrapped his arms and legs around Dean and pushed back against the thick cock. Dean reached in between their bodies to grasp onto Castiel’s smaller cock. The boy whimpered and tried to thrust into Dean’s fist.

“You’re so eager, baby,” Dean stated with an approving grin. He practically bent the boy in half and started to slam into him. Castiel moaned loudly and dug his fingernails into Dean’s back. He dragged them down against his back and left red scratches behind.

“I missed you so much!” Castiel cried out. Dean was slamming his prostate and knocking the air out of his chest. His small cock jumped and came all over Dean’s hand and his stomach. His body started to shake from the sensitivity. He heard Dean groan and felt his knot tying them together. Castiel whined and hugged Dean closely.

Dean flipped them over so that Castiel was laying on his chest. He patted the boy’s back and kissed his forehead. “I missed you too, Cas.” The boy looked at him with a dazed smile and placed his head on Dean’s chest.


	24. Relaxing

**Summary for the Chapter:**

> Castiel decides to take a hot bath.

**Notes for the Chapter:**

> Day 24 of Kinktober - Shower/bath

Castiel took off the fluffy robe and got into the tub. He groaned as the hot water cane in contact with his skin. He leaned his head back and closed his eyes. It was snowing outside which made the house very cold inside. Dean turned on the heater but it still wasn’t enough for Castiel, so he made his boyfriend buy hot cocoa for them. Hopefully that will warm him up. While Dean went out shopping Castiel decided to take a hot bath. It felt so good he didn’t want to leave or move to scrub himself. He felt sleepy and determined that he only needed five minutes.

A soft snore came out of him when someone knocked on the door. He startled awake and hit his head against the wall. He winced and rubbed his head with a wet hand. “Good morning sleeping beauty,” Dean said and grinned at Castiel. He stepped into the room and winked at his boyfriend.

“Where’s the hot cocoa?” Castiel asked.

“In the kitchen. I was going to ask if you wanted some right now, but then I see you taking a bath right now. Well, more like taking a nap in the bathtub.” Dean chuckled. Castiel looked so adorable. Now that he’s awake his boyfriend looked hot.

“I became very sleepy. I was so cold! You weren’t here to cuddle me!” Castiel pouted.

“Because I was getting the hot cocoa you wanted!”

“Yeah, I know.” Castiel sighed as he leaned his head back against the wall he raised a hand from the water and beckoned for Dean to come in. The man smirked and started to strip out of his clothes. Once he was done he climbed into the tub behind Castiel and sat down to wrap his arms around him. Castiel smiled and leaned back against Dean. He felt even more sleepy and just wanted to fall asleep in Dean’s warm arms. Before he could do just that though he felt something poke the small of his back. He shifted and felt Dean’s arms tense around him. He smirked wickedly when he found out it was actually Dean’s cock.

He grinded against Dean’s lap and let out a sigh as he felt his cock slide against his asscheek. He bit down on his bottom lip and leaned his head back against Dean’s shoulder. He gripped the man’s arms for leverage. Dean patted his leg and lifted him up. Castiel reached behind himself and grabbed Dean’s cock. He slid down onto his girth and moaned loudly. They had sex their morning and Castiel was still stretched out. It was better since he was so eager. He gripped the ends of the bathtub and rocked back against Dean.

“Mmm baby.” Dean gasped he gripped Castiel’s hips. He helped his boyfriend ride him and his toes curled. He always loved how tight his boyfriend is. Sometimes Castiel even liked the pain when he wasn’t stretched wide enough for Dean’s cock. The water splashed against their bodies and onto the floor. They ignored it as Castiel slammed down harder with each other thrust.

“Oh fuck, Dean!” Castiel arched his back and Dean licked his lips at the sight of his boyfriend. He always looked so beautiful when the man rides him. Dean would just sit back and let Castiel control the movements. Plus, it was harder for him to move in the bathtub. They were just too eager to go into the bathroom. At least they didn’t have to worry about cleaning up. Dean reached around Castiel and started to stroke his cock.

Castiel’s moans started to grow louder as he reached his peak. He came all over the shower wall and slumped against Dean. Dean thrust up against him a couple of times before pulling out. He stroked himself until he came with a muffled groan. He buried his face into Castiel’s hair and held him close to his chest. They laid down in the water for a while until they came down from their high.


	25. I Love your Scent

**Summary for the Chapter:**

> Dean can scent when Castiel is home.

**Notes for the Chapter:**

> Day 25 of Kinktober - Olfactophilia

Castiel walks through the front door of his house and closed it behind him when he enters. He spotted Dean on the couch and smiled. He waits by the front door for a few minutes to just observe Dean. The alpha’s eyes darts around the room and he raised his head to sniff the air. He turned his head towards the door but his eyes weren’t on Castiel. “I can smell you, Cas.” Dean said.

The omega giggled and walked over to Dean. The alpha held out his arms and motioned for Castiel to come closer. He slipped into Dean’s lap and wrapped his arms loosely around his neck. Dean’s hands started to roam his body and tried to figure out what outfit he wore to work today. He tugged on the tie and frowned. “Why are you wearing a monkey suit?”

Castiel laughed and kissed Dean’s nose. He looked extremely surprised at the gesture but smile anyways. “Today was my interview for that new job I wanted. I think I nailed it.” He started to draw random symbols on Dean’s bicep subconsciously as he looked into Dean’s eyes that weren’t in focus. He loved them so much and always told Dean about it. He was always insecure about his disability. It made him feel less like an alpha since the others would pick on him for it. Castiel didn’t care though. Dean was sweet and gentle. A man who deserved so much more.

“The daycare?” Dean asked excitedly. They would sometimes pass by so that Dean could hear the children’s laughter and smell their mixed scents from their parents. It always brought a warm smile to his face. They both wanted kids so much, but Dean was still hesitant about it. Castiel understood why.

“Yes. They’re going to call me in two to three days. Let’s just hope I get the job.” Castiel smiled happily. He loved kids so much. Maybe this job can help him with what he doesn’t have. It wasn’t Dean’s fault. He was patient. They both were. They just had to wait for the right moment. Plus, Dean looked so happy at the news. He wrapped his arms around Castiel and pulled him closer. He nuzzled into the crook of his neck and breathed in his scent. He sighed quietly and lapped at the scent glands which made Castiel moan quietly.

Dean was obsessed with his scent. Even though he never saw how Castiel looked he didn’t care. He had a beautiful personality and an intoxicating scent Dean can’t get enough of. He had a picture in mind at how Castiel looked, but he didn’t how if he was accurate. It didn’t matter. His omega was beautiful inside and out no matter how he looked. He breathed in his scent and felt himself get hard from the sweetness of it. He panted heavily and left saliva on Castiel’s neck. The omega wrinkled his nose and chuckled quietly. “Oh, alpha.” He cupped Dean’s cheeks and squished them with his fingers.

“I’m trying to be sexy here while you’re trying to be adorable.” Dean shook his head just slightly but was smiling anyways. His pupils were blown wide just from scenting Castiel. The intense gaze he gave the omega made him slick. He shivered in Dean’s grasp and sighed quietly. He wasn’t paying attention to his own arousal though.

Castiel slipped a small hand in between their bodies and started to unbuckle Dean’s belt. The alpha opened his mouth to say something but Castiel silenced him before he could get a word out. He took out the alpha’s cock and stroked him with one hand. He shoved his other hand into Dean’s hair and pressed his nose against the scent gland again. The alpha growled quietly and scent Castiel. His moans sounded wounded but he was actually enjoying himself. He lapped over the omega’s scent gland a couple of times to taste him.

Castiel’s hand couldn’t fully wrap around Dean’s cock but he tried. He petted Dean’s hair and stroked him towards his orgasm. The alpha’s knot popped and he groaned loudly as he covered the both of them in his own semen. “Good alpha.” Castiel giggled as he ruffled Dean’s hair and kissed all over his face.

“You should be at least taken off the monkey suit.” Dean said weakly.

“I know, but you were already getting me all hot and bothered.” Castiel smiled as he patted Dean’s cheek. “I love your eyes by the way.”

Dean grinned, “I know.”


	26. Is it a Miracle?

**Summary for the Chapter:**

> The witch must’ve gave Castiel a gift.

**Notes for the Chapter:**

> Day 26 of Kinktober - Lactation

The witch grabbed her spell book and jumped through the window before the Winchester brothers could burst in through the door. She landed on the ground smoothly and made a run for it. She heard footsteps behind her and ran even faster. He looked behind her then looked back. A man with a gun stood in her way. He aimed it at her and shot her a couple of times. She was able to dodge the bullets but just barely. She glared at the man and muttered a spell under her breath. The man’s eyes widened, and he crumpled to the floor with a loud groan. He clutched his belly and whimpered softly as the witch got away.

Dean knelt down beside Castiel while Sam went ahead of the pair. “Hey, Cas. Look at me, baby.” He patted his cheeks a couple of times and frowned when he saw tears. Castiel cried quietly and curled on himself. Whatever spell the witch cast on him was giving him bad stomach cramps. “Stay with me, Cas. You’ll be alright.” Dean’s voice wavered as he rubbed Castiel’s back. Castiel felt around for Dean’s hand until he found it. He squeezed it tightly and Dean had to bit back his protest. He was most likely going to break Dean’s hand.

A few minutes later it was over. Castiel slumped on the ground and let go of Dean’s hand. He sighed quietly and wiped the tears away. The pain went away just as Sam came back empty handed. “She got away,” he announced with a frown.

“She did something to Cas.” Dean said as he helped Castiel up who practically cling to him. He patted his back awkwardly and just let it happen. Even when they walked back towards the car. The brothers were listing down any possible spells the witch must’ve cast on Castiel. He was extremely quiet while they talked. They knew he was quiet just not  _ this  _ quiet. When Dean tried to pull away from Castiel the newly human’s grip tightened on him. “Uh...Cas. I have to drive.”

Castiel looked up at Dean then at the car before letting go of him. He looked down at the ground as he shuffled towards the impala and climbed into the backseat. The brothers looked at each other in confusion. Dean was mostly worried. He would ask Castiel when they get back at the bunker. Thankfully the witch was close by their place. They climbed into the car and Dean drove them back to the bunker.

-

When they arrived, Castiel immediately made a beeline towards the kitchen. He looked through the cabinets and drawers until he found what he was looking for; the Nutella. He grabbed a spoon and opened it before dipping the spoon in to eat the chocolate. Dean followed the newly human and raised an eyebrow when he spotted him covered in chocolate with an empty Nutella bottle in hand.

“Are you okay?” Dean walked closer and took the empty bottle and spoon away from Castiel.

“No.” Castiel blurted out as he opened the freezer and grabbed the tub of ice cream. He wrenched it open and grabbed another spoon. A much bigger one to scoop up the ice cream and eat it. Some of it dripped out of his mouth. Dean made a dirty face and shook his head.

“There are plates, you know.” Dean tried to take away the ice cream, but Castiel turned his back towards him.

“I’ve been craving sweets since I got into the impala. Now that I have it I won’t let you take it away from me.” Castiel hissed at him and cradled the ice cream.

“Fine. Are we going to talk about the spell the witch cast on you? Did she make you hungry or something?” Dean chuckled. “That would be funny.” Castiel stared at Dean in silence before bursting into tears. Dean was so surprised he stood there in shock for a few seconds before the gears in his head started to car. “Cas what’s wrong? Are you okay?” He grabbed Castiel’s biceps and frowned at his puffy face.

“Y-you laughed at me!”

“What? No I wasn’t! I wasn’t laughing at you, baby.” Dean wrapped his arms around Castiel and hugged him tightly. He ignored the cold ice cream in between them and rubbed Castiel’s back gently. They stayed there and Dean tried not to pull away from how cold his belly was getting from the ice cream.

Once Castiel was calmed down he pulled away and handed Dean the tub of ice cream. “I’m going to shower.” He wiped the tears away and left the kitchen. Dean glanced between the ice cream and Castiel walking away. He was trying to figure out what the hell happened.

He didn’t have to wait long since he heard Castiel scream out his name. “Coming!” Dean called out as he placed the ice cream back into the freezer before walking towards the bathroom. He knocked on the door and Castiel opened it. He grabbed Dean’s arm and pulled him in before slamming the door shut. He had a towel wrapped around his body and his cheeks were flushed. “What happened?” He asked slowly as he stared at Castiel who looked embarrassed.

“I-I think I know w-what that witch did to me.” Castiel whispered as he stared at the wall behind Dean.

“Okay. Well, what did she do?” Dean raised an eyebrow.

Castiel frowned and sighed quietly. He tugged the towel off and let it pool around his ankles. Dean was still confused until he lowered his eyes towards the problem. So many thoughts were going through his head. “Oh, you’re on your period.” He blurted out without thinking.

Castiel grabbed the towel and wrapped it around himself again. “Dean! This is serious! I have a vagina! A bleeding vagina! I’m going to die!”

“Calm down, baby. You’re not going to die. The bleeding will go away next week. If you’re lucky then in a couple of days.” Dean smiled awkwardly. He tried to stay calm so that Castiel wouldn’t freak out. This isn’t the weirdest thing he has seen before. “Just take a bath. You’ll feel much better.”

“You’re going to take a bath with me though.” Castiel said as he started to take off Dean’s clothes before a hunter could say a word. He just like it happen. Whatever to make Castiel happy.

The next few days was tough for the pair. Dean had told Sam about the problem and the younger Winchester was looking for the witch while Dean took care of Castiel. He got stuck in watching chick flicks and trying to take away food from Castiel because the man kept stuffing his face every hour of the day. The worst part of the day was seeing Castiel staring at a wall with a blank expression. It meant he was thinking about the dark thoughts lurking in his mind. During those times, Dean made sure to not leave his side. Not even for a second. Castiel kept him up late because of how clingy and a cry baby he is, but Dean wouldn’t change anything about their time together.

One day, Sam went out on his own; stating he had a lead on the witch. Dean and Castiel were snuggled up in Dean’s bed watching a movie. Castiel was getting bored of the movie and wanted to do something else. He always loved watching new movies with Dean but not right now. He was horny. His stupid hormones must be acting up now. He was done with his period two days away. It didn’t last very long thankfully. Castiel didn’t think he could’ve survive much longer. He glanced over at Dean who was engrossed with the movie. He turned his back towards the hunter and laid there for a couple of seconds. When Dean didn’t notice he covered his body with a blanket and shoved a hand down his sweatpants. He rubbed a dry finger against his pussy and bit back a moan.

Castiel was much more sensitive with a vagina he learned quickly. He was already soaking wet. He pushed a finger inside himself and covered his mouth with his other hand. He rubbed his clit and bit down on his hand to keep from moaning so loud. He started to rub the clitoris with two fingers which sent a shock throughout his body. It felt so good he didn’t want to stop. He was so out of it he didn’t notice the bed squeaking until Dean tugged his hand away from his mouth. Castiel’s eyes snapped open, and he looked into Dean’s green lustful eyes. “Hey, baby. Having fun without me?” Dean smirked.

Castiel blushed and broke the eye contact with Dean. He wasn’t even sure if Dean would do any sexual activities with him being...different. He looked back up at him and smiled nervously. “S-sorry. I didn’t think you would want to do anything with the current situation…” He tried to pull away but Dean’s grip tightened.

“Don’t think like that. I don’t care how you look or what you have. I love you for you, and who knows; maybe this can be one of our kinks.” Dean wiggled his eyebrows suggestively and grinned. “Less money to buy lube since a vagina self lubricates.” He winked.

Castiel blushed even more and nodded slowly. “I suppose…”

“Just tell me if you don’t like that, okay?” Dean raised his eyebrows and waited for Castiel to nod. He tugged off the blanket and stripped them out of their clothes.

Once they were naked Dean reached a hand in between Castiel’s thighs and start to play with his pussy. Dean’s fingers were skilled when they rubbed against his cunt. Castiel’s legs started to shake in anticipation, and he moaned loudly. He was leaking by the time Dean started to thrust fingers inside his pussy. He screamed and arched his back when Dean prodded his G spot. “Dean!” He sobbed as he gripped the sheets.

“Feels good doesn’t it?” Dean asked. He pulled his fingers out and coated his cock with Castiel’s juices. He pushed Castiel’s legs towards his chest and slapped his cock against his pussy. Castiel’s hair stuck to his forehead and his legs were shaking in the air. Dean teased his slit for a bit before pushing into him. He moaned loudly. “Your cunt is so tight, princess.” His thrusts were smooth with the fluid Castiel’s pussy was providing. High pitch moans were fucked out of him.

“Dean! Deeeeeaaan!” Castiel cried out. He gripped Dean’s arms and felt his walls clench around the hunter’s cock. He threw his head back against the pillow and panted heavily. When Castiel came his body started to shake when Dean kept assaulting his G spot. “Ah! Ahhh!”

Dean came inside of Castiel with a groan and left his soft cock inside him. Castiel felt Dean’s cum fill him up and leak out of his pussy. He had a dazed smile on his face as his eyelids started to droop. He felt Dean kiss his forehead and sighed quietly.

-

**8 months later.**

“Where is my ice cream?!” Castiel called out to Dean. He had been craving it all morning and the stupid hunter still wouldn’t give it to him. Dean walked inside the room with a bowl filled with ice cream and sat down on the bed to feed Castiel. He leaned forward and wrapped his lips around the spoon. He moaned as the cold ice cream flooded his taste buds. He rubbed his big round belly and hummed.

Sam never found the witch which meant she couldn’t undo the spell. Castiel didn’t seem to mind because he was rubbing his round belly lovingly. If Castiel was happy then Dean was happy. Even though he had to feed Castiel whenever he demanded it. He didn’t mind though. Once Castiel was done with the ice cream Dean set the bowl down and stood up to kiss Castiel. He sighed quietly and kissed him back.

“Dean?” Castiel whined. “They hurt again.” He looked down at his big breasts that were filled with milk for their baby. They started to grow when he found out he was pregnant. Dean thought it was odd at first, but eventually the both of them thought it was a miracle. They were going to be a family. Something they always wanted.

Dean smirked and helped Castiel out of his shirt. He rubbed over his belly before leaning in to lap at his nipples. Castiel moaned quietly and slid his hands into Dean’s hair. The hunter wrapped his lips around a nipple and sucked on it. Milk flooded his mouth, and he drank it up eagerly. Castiel moaned quietly and tugged on his hair gently. Dean moaned onto the other nipple and teased it with his teeth gently. He also sucked the milk out of that breast and drank it all. He kissed Castiel’s chest and moved towards his neck and finally his mouth.

“Better?” Dean murmured.

“Yes. Much better. Thank you, Dean.” Castiel smiled lovingly at him.


	27. A Place we Don’t Belong in

**Summary for the Chapter:**

> Day 27 of Kinktober - Against a Wall

Dean stared down at his desk of cards when he heard his cell open. He looked up and saw his new roommate walking into the area. He looked young. Like a kid who didn’t belong here. He was also very scared and tried to avoid Dean’s gaze as he sat down on the bottom bunk. Dean was dangling his legs from his position on the top bunk and jumped down. He set the deck of cards down and glanced at the boy. “What are you in for, kid? Stealing?” Dean joked and chuckled to lift his spirits up just slightly.

The boy finally looked at him then looked away just as quickly. “No…” he said it so quietly that Dean barely heard him. “I’m a hacker, and the police raided my house to arrest me.” His voice wavered a bit and he took a couple of deep breaths to keep from crying. He was scared. He didn’t want to be here.

“That’s tough…” Dean trailed off. He wasn’t very good in comforting others and didn’t quite know how to handle a crying kid. He reached out and patted Castiel’s back awkwardly. “Word of advice; always shower alone and don’t sit next to anyone.” He pulled his hand away and went back to his shuffling his cards. Castiel’s eyes widened in fear and his body shook. He wasn’t going to make it out alive.

-

In the course of two weeks Dean decided to take Castiel under his wing. Only because the kid kept asking stupid questions and hiding behind him everywhere they go. Some of the other prisoners were eyeing him like a piece of meat. None of them made a move on him though. Only because they knew Dean was strong enough to fight them all off. He knew how to fight so Castiel was safe with him. The kid wasn’t going to give up anyways. Not until Dean agreed to protect him fully.

“What are you in for? I never asked you.” Castiel asked him one day while they were playing cards.

“Identity theft, credit card scams, and grave digging.” Dean said it so casually as if talking about the weather. Castiel was shocked and Dean had to snap his fingers in front of his face. “Your turn.”

“O-oh…” Castiel stammered as he placed a card down. He wanted to ask more questions but refrained himself. Dean didn’t seem it was important so he kept his mouth shut.

A guard came by their bell and tapped his baton against the gate. “You two are on laundry. Get moving!” He unlocked the cell and opened it. Both inmates placed their cards down, facing down, before standing up and following the guard into the laundry room.

The guard stood outside as Dean and Castiel stepped into the room. Castiel frown and wrinkled his nose at all the dirty orange jumpsuits in the room. He glanced over at Dean who started to opened the washing machine and stuff clothes into it. Castiel glanced over to the guard outside then at Dean with an idea in mind. He walked over to Dean and tugged on his arm to lead him to the dark corner of the room.

“What are you doing, Cas?” Dean questioned and raised a brow. Castiel shushed him until they were in the dark corner. He turned towards Dean and brought his head down for a kiss.

“We finally have some privacy.” Castiel bit his lip and grabbed the zipped to tug it down.

Dean gripped his hand before he could further. “Are you sure?”

“Oh, definitely!” Castiel smiled. Dean searched his face for any hesitation before letting go of his hand. Castiel unzipped Dean’s orange jumpsuit and tugged it off his muscular figure. He roamed his hand over Dean’s chest and broad shoulders. Oh, he really loved what he saw.

Dean practically broke the zipper when he tried to take off Castiel’s jumpsuit. He kissed him again and picked him up from the floor. Dean pinned him against the wall and lapped at the column of his neck. He sucked dark bruises on his pale neck and rubbed a finger against Castiel’s soaked opening. “You opened yourself up. Good. I’m not patient.” Dean growled. Castiel mewled and leaned his head back against the brick wall. He felt himself sink onto Dean’s cock and sighed quietly. He wrapped his legs around the older man and grounded against his lap.

“Please move. I need to cum so bad.” Castiel panted. He was waiting for so long to find some privacy for them. He didn’t like giving a show to others. He was too shy for that. Dean fucked into him and Castiel bit his lip to keep the moans in. His back scrapped against the brick wall and there was no doubt he would have red scratches on his back by the end. He wrapped his arms around Dean’s neck and held on for dear life as the man rammed his prostate.

He cried quietly and his lithe body started to shake. When Dean brushed a hand against his cock strips of cum spurted out of him. He tensed up in Dean’s grasp and clenched around the thick cock inside him. The older man groaned quietly and sunk his teeth in Castiel’s shoulder as he came inside the boy. He sighed quietly and winced when he was set down on the ground. He held onto Dean’s arms as his legs shook from the intense orgasm.

“Oops.” Castiel smiled awkwardly up at Dean. All Dean did was smile back at him.


	28. Sweet Dancing

**Summary for the Chapter:**

> Mobster Dean decides to buy the stripper instead.

**Notes for the Chapter:**

> Day 28 of Kinktober - Stripping/Strip Tease

Dean walked into the dark room and gave his eyes a minute to adjust. The man in the room lit up a math to lit the candles spread out throughout the room. Dean quirked an eyebrow and gave the man a weird look. He decided to not ask questions with the man’s bodyguards blocking the exit.

“Dean! It’s a pleasure to finally meet you. My name is Alastair.” The man grinned as he held out a hand. Dean was creeped out with him immediately. He gave out a weird and dangerous vibe Dean wouldn’t want to mix in with. He gripped the man’s hand and shook it. When they pulled away he wiped his hand on his expensive slacks and wrinkled his nose in disgust. “Please, sit.” He gestured at the seat in front of him.

Dean took a step forward and sat down on the seat. He took off his fedora hat and placed it on his lap. “I didn’t come here for friendly talk, Alastair. I just want what you have.”

“Straight to the point, I see.” He smirked. He went under the desk to retrieve the box and set it on the desk. He hoped it with delicate hands and showed Dean the diamond necklace. The mobster leaned in and observed the shining necklace with an approval nod.

“It does look real, and here I thought you were lying about it.” He sat back in his seat and smirked. He knew for a fact that the necklace in the box was a fake. His fellow ‘friend’ Crowley was right. He was just acting dumb and wanted to see how this would play out.

Alastair seemed pleased with his response. He opened his mouth to voice his price when he was interrupted by the door opening. He slammed it shut and glared at the man who walked inside. It was one of the strippers Dean saw when he came in through the building. Why did Alastair own a stripping club? He didn’t know. Maybe for the man’s pleasure which wasn’t very appealing to Dean. The man looked young and he was practically wearing nothing except for the crop top and thong he had on. He glanced between the two men talking then looked down at the floor.

“What is it, Castiel?” Alastair asked with an irritated expression.

“I-I was wondering if I could pick up my paycheck now?” Castiel squeaked out.

“We’ve talked about this. You’ll get it next week. Can’t you see I’m in a meeting?” He gestured between Dean and himself.

“I-I see that. It’s j-just I haven’t paid my rent, and I need it really badly.” Castiel looked like he was about to have a mental breakdown right in front of him. Dean felt pity for him. Most of the strippers here needed the job to have a living, so he knew how that was like.

“I don’t care. I don’t have the check right now. Unless…” Alistair smirked, “you’ll give me what I’ve been asking for since the first time I laid eyes on you.” The fear of Castiel’s expression was clear on his face at the suggestion. Dean almost felt sick. Especially since he was right in front of them. The man looked like he was considering it. Anything to have a roof over his head.

“I think I found a better thing to buy.” Dean said before Castiel could voice his thoughts. He glanced at Alastair then reached into his pocket for his checkbook. He filled out a check and handed it over to Alastair. “That much money for Castiel here.”

“For one night?” Alastair asked with a raised eyebrow. This was so much money for one night with one of his strippers.

“I’m buying him.” Dean said straight out. He knew how Alastair treated all the people here. He treated them as slaves who does everything for him. The amount of research and breaking of fingers Dean had to do to get that sort of information. At least he would be doing the man a favor. Castiel didn’t look too comfortable to want to be a stripper.

“Hmm…” Alastair rubbed his chin as he stared at the check and then up at Castiel who looked a little hopeful. “Fine. This will do.” He folded up the check and slipped it into his pocket. Castiel felt like he was about to burst with joy. He was free. He didn’t have to be under Alastair’s control anymore.

“It was a pleasure to do business with you, Alastair. I must go now.” Dean stood up from the chair and put his fedora hat back on. He started to walk away and Castiel scrambled to follow him. He gripped onto Dean’s sleeve and followed him out of the building.

-

When Dean drove them home Castiel didn’t know what to do now. Dean had lend him his jacket when they left the stripping club. He didn’t know if he was supposed to give it back and leave or stay. He so badly wanted to stay. Dean answered his question when he beckoned the man into his house. It was a rather huge house. Too big for just one man to live in.

“Don’t be shy.” Dean smirked as he walked over to the living room. He sat down on the couch and grabbed the remote to turn on the stereo. Castiel walked into the living slowly and smiled slightly at the music playing. Dean had his legs spread out in front of him as he stared at Castiel with an intense gaze.

The man froze for a couple of seconds before springing into action. He took off the jacket and placed it on the couch before walking over to Dean to stand in front of him. The mobster was an attractive man and Castiel could get used to this. He swayed his hips to the beat of the music. He grabbed the hem of his crop top and took it off slowly. Then he moved onto taking off his tong. He walked over to Dean seductively and sat down on his lap. He grinded his hips and sighed softly.

Dean gripped his hips and rubbed his hard clothed cock against the crack of Castiel’s ass. The man moaned softly and dropped his head on Dean’s shoulder. The mobster growled softly and flipped them to pin Castiel to the couch. “I’m about to rock your world baby.” He smirked.

“I can’t wait.” Castiel smiled.


	29. The Tracks to a New Beginning

**Summary for the Chapter:**

> Dean gets on a train and meets Castiel.

**Notes for the Chapter:**

> Day 29 of Kinktober - Double Penetration

The sound of the movement coming from the train made Dean have motion sickness as he tried to read the book he had. He tried laying down and it worked, only for a bit. He shut the book and sighed as he sat up. He placed it on the bed and frowned down at his phone. Hardly any time passed. He looked out the window and laid his head against it. He watched the trees go by in the middle of nowhere.

His eyelids started to droop when he heard a moan. He lifted his head off the window and glanced towards the door. The last time he checked he was the only one occupying this part of the train. He wanted his privacy and silence. He stood up from the bed slowly and heard another moan. It was quiet and muffled. He walked out of his room and looked around the train. He walked down the area and glanced towards the shut door. He knew he shouldn’t be interrupting anything but the person was too loud. He was just assuming this guy was working out or doing yoga. He didn’t realize how wrong he could be.

He turned the doorknob and pushed open the door. The sight in front of him made him trip over the shoe that was nearby the entrance. The man on the bed stopped his movements and stared at Dean in shocked but mostly with embarrassment.

It was the man named Castiel who Dean was talking with when he first stepped onto the train. He was an attractive man Dean would love to ask on a date.

Castiel was naked and had a dildo up his ass. He had a hand over his mouth and he was frozen in place; staring at Dean. He scrambled to get up from where he was fallen and closed the door behind him. He swallowed thickly and roamed his eyes across the beautiful body. “Hey,” he said weakly and licked his lips. He couldn’t stop himself from advancing until he was practically kneeling on the bed.

“Hi…” Castiel removed his hand from his mouth and blushed.

Dean placed a hand on Castiel’s knee and the man fluttered his eyes shut at the touch. He felt the dildo move inside of him and moaned loudly. Dean was thrusting the dildo in and out of Castiel. He brought another hand towards his hole and started to stretch him out even more.

“O-oh!” Castiel moaned and threw his head back against the pillow. Dean added more fingers and pushed against Castiel’s walls.

“I’m going to try something.” Dean whispered. He looked into Castiel’s blue eyes and saw nothing but trust in them. The man nodded and gripped the sheets tightly as he waited for Dean to finish stripping out of his clothes.

Once Dean was naked he grabbed the dildo again and pressed it against Castiel’s walls. He rubbed the head of his cock on Castiel’s hole before pushing in. He screamed and squeezed his eyes shut at the slight burn of the stretch. He panted heavily and looked dazed. He didn’t even know he could stretch that much, and it felt so good. Dean moved slowly at first and then picked up his pace. Castiel became a moaning mess and his hair stuck to his forehead. The blush spread through his chest as he was pounded into the mattress.

“Yes!” Castiel moaned and gripped Dean’s strong biceps. He dug his fingernails into the skin and looked up at the man. They stared into each other’s eyes until they both came.

Castiel winced when Dean pulls out of him. His whole body twitches when Dean pulls out the dildo. He moaned quietly and felt his eyelids droop. Dean laid down on the bed and wrapped his arms around Castiel. He could get used to this for the rest of the train ride.


	30. Dean Doesn’t Share

**Summary for the Chapter:**

> The mermaids take a sudden interest on Castiel.

**Notes for the Chapter:**

> Day 30 of Kinktober - Stockings/Tights/Pantyhose

Dean practically dragged Castiel to the pond where the mermaids were at. He looked over at the boy to see his reaction. He wasn’t disappointed. Castiel had a huge smile on his face and a look of wonder as he watched the mermaids. Some of them were styling their hair, some were swimming around, and some were even playing games with each other. It was truly amazing to see mystical creatures in this island. He looked at Dean then back at the mermaids before running towards the pond. He knelt down on the grass and reached out to touch the water.

One of the mermaids spotted him and swam towards him. “Hey, handsome,” she said with a smile. “I love your dress. Where did you get it?”

Castiel looked down at the baby blue dress he was wearing and fiddled with his fingers nervously. He was always shy around new people. “My mother gave it to me. We didn’t have enough money to buy me new clothes, so she decided to just give me my sister’s.” He padded down the dress and smiled back at the mermaid. “I didn't mind. It’s quite comfortable.”

More mermaids were swimming towards him. He was the center of attention which made him flush. One of the mermaids sat next to him and placed a flower crown on top of his head. “I love your style,” she said and grinned at him. She placed a hand on his shoulder and Castiel frowned as he felt his dress getting wet from her touch.

Meanwhile, Dean was burning up with jealousy and irritation. He hated how all the mermaids were swooning over him and Castiel was giving them his full attention. He walked up to them and cleared his throat loudly to grab their attention. “Ladies. Ladies. Give Cas some space.” One of the mermaids splashed Dean with water and all of them screeched with laughter at Dean’s expression. He was surprised but mostly annoyed at the childish thing they did. He grabbed Castiel’s arm and lifted him up from the ground. He turned him around and pushed him away from the pond. “See you dicks later.”

“Aw, come on! Give him back!” The mermaid who splashed Dean pouted up at him. The rest joined in at the whining. He was still walking away and ignored Castiel’s confused look.

Once they were out of sight, Dean looked towards Castiel and sighed in relief. “I didn’t think they would take a shine on you. They usually don’t. They always just ignore people,” he mumbled angrily.

Castiel frowned and reached out to grab Dean’s hand. He gave it a small squeeze. “They’re nice, but I didn’t like the attention they were giving me. It was too much for me to handle.”

Dean brought their hands up and kissed Castiel’s hand. “Yeah, I know.” He kinda felt guilty that he broke Castiel away from the mermaids because of his jealousy instead of Castiel’s comfort.

“I see that look on your face. Whatever you’re thinking; stop it.” Castiel glared at him then smiled afterwards. He stroked Dean’s knuckles with his other hand.

Dean smiled back at the boy and felt better immediately. Castiel always had that effect on him. He leaned in and pecked the boy on the lips. Castiel followed his lips and kissed them back but more deeply. Dean moaned quietly and wrapped his arms around Castiel loosely. Dean walked backwards and his heel hit a rock, making him stumble onto the ground with Castiel. They looked at each other in surprised then burst out laughing. Castiel tried to muffle his laugh by kissed Dean’s neck and his face. Once Dean had his laughter under control he flipped them over and pinned Castiel to the ground.

He sat back and lifted one of Castiel’s legs. His hand roamed over the pantyhose Castiel was wearing and rubbed his cheek against the soft material. He grabbed his other leg and lifted them up. Castiel gripped the back of his knees and held his legs open. Dean rubbed Castiel’s crotch then ripped open the pantyhose. He slid the underwear aside before diving in to lick along Castiel’s sensitive hole.

The boy dropped his head against the grass and moaned. His legs shook as Dean licked along his sensitive walls. The boy prodded his rim until his tongue breached the ring of muscle. Castiel let go of his legs and they landed above Dean’s shoulders. He didn’t seem to notice because his devilish tongue didn’t stop. Castiel was able to heard the loud slurps and moans Dean was making, but they weren’t as loud as the noises Castiel was making. When Dean brought a hand up to rub Castiel’s cock through the pantyhose he couldn’t hold it anymore. He came with a scream and tried to get away from Dean’s tongue.

Dean stood up and kissed Castiel’s sweaty forehead. The boy wrinkled his nose in disgust when he shifted. “Yucky. I need to change.” He pouted.

Dean chuckled quietly and kissed the pout away. “I’ll lend you my clothes.”


	31. Happiness

**Summary for the Chapter:**

> They both try to please each other.

**Notes for the Chapter:**

> Day 31 of Kinktober - Deep-throating/Size difference/Lactation

Castiel rocked his pup to sleep and placed him on the crib. He cooed softly and smiled at Jack’s tiny sleeping form. He reached out and stroked his cheek softly. He pulled away and walked out of the dark nursery room. He closed the door behind him and walked towards the master bedroom. He spotted Dean on the bed. Already under the covers with his glasses on as he read a book. From Castiel’s position he could tell the alpha was already naked. He wasn’t wearing a shirt and the thin sheet covered nothing. Castiel untied his robe before climbing under the covers. He scooted closer to Dean and laid his head on his shoulder.

“What are you reading?” Castiel asked as he skimmed over the page.

“Before I Fall. One of my students wanted me to read it. I have to admit, it’s interesting.” Dean turned the page when he done reading the passage and bookmarked his page before closing it. He placed the book on the nightstand and smiled at Castiel.

“Let me guess; is the student a certain blonde omega who keeps trying to get at you?” Castiel rolled his eyes.

Dean chuckled and lifted Castiel’s chin to kiss his lips. He took off his glasses and placed them on top of his book. “You have nothing to be jealous about.”

“Yeah, I know. She’s just really annoying and takes every opportunity to touch you. I don’t like it.” Castiel pouted. He laid a hand over Dean’s chest and hooked his leg around his hips. He was extremely possessive over his alpha. Especially when they finally started a family and the omega started to feel insecure about his body.

“I know. I know. Trust me; if I could kick her out of my class I would, but all the other classes are full.” Dean rubbed a finger over Castiel’s nipple lightly to pull a gasp out of him.

Ever since Castiel was pregnant with Jack his body started to change. It was getting prepared to give birth to a pup. He had curves and his chest started to swollen with breasts for the milk he was producing. No alphas liked omegas who already have children. They both were happy no other alpha bothered Castiel ever again, but there were omegas who draped themselves all over Dean. It irritated Castiel, but it mostly made him insecure.

“You’re overthinking again,” Dean sighed. He rubbed Castiel’s back with his knuckles gently and kissed his brow.

“I’m sorry. I just can’t help it,” Castiel mumbled sadly.

Dean was determined to show his mate how much he loved him. He wiggled out of his grip and climbed on top of him. He dipped his head to kiss along a column of Castiel’s neck and went lower until he sucked a nipple into his mouth. He moaned when the milk flooded his taste buds. He drank it up quickly before moving onto the next nipple. Castiel buried his hands into Dean’s dirty blonde hair and moaned quietly. His eyes fluttered shut and he arched his back at the sensitivity of his nipples.

When Dean lifted his head up milk was dripping down his chin. He was hard at such fondling with his mate’s breasts. Castiel sat up and pushed Dean onto his back. He wrapped his small hands around the alpha’s huge length and stroked him roughly. Dean’s breathing immediately picked up and he dropped his head on the bed.

Castiel wrapped his lips around the head of the alpha’s cock and bobbed his head slowly. He took as much of Dean’s length as he could. He thrust into the omega’s mouth who gagged and pulled away. He wiped away the saliva and returned to sucking Dean’s cock. This time he was much more prepared when the alpha thrusted into his mouth. Dean grabbed a handful of Castiel’s black hair and shoved his head down. Tears of pleasure streamed down Castiel’s cheeks and spots of black started to flood his vision.

Dean let go of him and Castiel pulled away to take deep breaths. His small cock was dripping pre cum just from sucking his alpha’s cock. He was shaking with excitement as he saw the knot swelling. He squeezed it with his hand and saw Dean’s whole body twitch. He wrapped his mouth around Dean’s cock again and let his mate face fuck him.

Dean planted his feet on the bed and thrusted roughly into Castiel’s mouth. He groaned loudly as he lost himself in his thrusts until his knot popped in the omega’s mouth. Castiel squeezed his eyes shut as he tried to drink up every last drop of Dean’s cum. Some of it dripped down his chin but the alpha looked pleased. He patted Castiel’s cheek lovingly and ran his fingers through his thick hair.


End file.
